Synthesis of phenylethanolamine

Preparation of phenylethanolamine

Preparation of phenylethanolamine by reduction of mandelonitrile with sodium amalgam

Preparation of phenylethanolamine by reduction of of mandelonitrile with sodium amalgam

Preparation of phenylethanolamine by reduction of of mandelonitrile with sodium amalgam

35 g of the mandelonitrile are dissolved in 550 ml of 50 % alcohol, chilled in a freezing mixture, and reduced with continual chilling and mechanical stirring, with 1400 g of 4 % sodium amalgam, on to all of which the solution should be poured. To complete the reduction requires several hours during this time the reaction is kept just acid to litmus by slowly dripping in first 50 % acetic acid, then the glacial acid, regulating the speed of addition by careful tests with litmus paper, as the reaction should neither be allowed to remain alkaline nor become strongly acid. When all of the sodium has been used up the solution is poured from the mercury and concentrated to about one-half volume. The solid mass of salts obtained on cooling is ground up in a mortar, thinned with a little dilute hydrochloric acid, filtered off, and washed with more of the dilute acid. The filtrate is shaken out with ether to remove non-basic impurities and is then covered with a layer of ether, made very strongly alkaline with sodium hydroxide, shaken out, and the extraction with ether repeated several times. The ethereal solution is dried over crushed sodium hydroxide and concentrated to small bulk.

An advanced laboratory manual of organic chemistry, M. Heidelberger, 49-50, 1923

Preparation of phenylethanolamine by reduction of benzoyl cyanide with lithium aluminium hydride

Preparation of phenylethanolamine by reduction of of benzoyl cyanide with lithium aluminium hydride

Preparation of phenylethanolamine by reduction of of benzoyl cyanide with lithium aluminium hydride

A solution of 7.35 g of benzoyl cyanide in 100 ml of dry ether was added dropwise to a stirred solution of 10 g of lithium aluminium hydride in 300 ml of ether so that refluxing was maintained. After another four hours of boiling the mixture was decomposed with water, and a 30% sodium hydroxide solution was added in small portions until a granular precipitate appeared. The reaction solution was filtered, washed with ether, and the oily residue from the combined ether layers was distilled under reduced pressure. It yielded 6.5 g or 86% of a colorless solid which, after recrystallization from benzene-petroleum ether melted at 56.5-58° C.

J. Am. Chem. Soc., 1952, 74 (21), pp 5514–5514

IUPAC Name

2-amino-1-phenylethanol

InChI

InChI=1S/C8H11NO/c9-6-8(10)7-4-2-1-3-5-7/h1-5,8,10H,6,9H2

InChI Key

ULSIYEODSMZIPX-UHFFFAOYSA-N

Canonical SMILES

C1=CC=C(C=C1)C(CN)O

MeSH Synonyms

2 Hydroxyphenethylamine, 2 Phenylethanolamine, 2-Hydroxyphenethylamine, 2-Phenylethanolamine, beta Hydroxyphenethylamine, beta Phenylethanolamine, beta-Hydroxyphenethylamine, beta-Phenylethanolamine, Bisnorephedrine

Depositor-Supplied Synonyms

2-Amino-1-phenylethanol, phenylethanolamine, 7568-93-6, 2-Hydroxy-2-phenylethylamine, Bisnorephedrine, Phenethanolamine, beta-Hydroxyphenethylamine, 2-Phenyl-2-hydroxyethylamine, alpha-(Aminomethyl)benzyl alcohol, beta-Phenethanolamine, 2-Amino-1-phenyl-1-ethanol, Phenylethanolamin, Ethanol, 2-amino-1-phenyl-, beta-Hydroxy-beta-phenylethylamine, .beta.-Phenethanolamine, (RS)-2-Amino-1-phenylethanol, (+-)-Phenylethanolamine, .beta.-Phenylethanolamine, 2-Amino-1-phenyl-ethanol, (+-)-alpha-Phenylglycinol, .beta.-Hydroxyphenethylamine, 2-amino-1-phenylethan-1-ol, Phenethylamine, beta-hydroxy-, .beta.-Hydroxyphenylethylamine, alpha-Aminomethylbenzyl Alcohol, Benzenemethanol, .alpha.-(aminomethyl)-, Benzeneethanamine, beta-hydroxy-, beta-Phenylethanolamine, Phenethylamine, .beta.-hydroxy-, Benzeneethanamine, .beta.-hydroxy-, NSC 5021, .alpha.-(Aminomethyl)benzyl alcohol, NSC 46837, Benzyl alcohol, alpha-(aminomethyl)-, Benzenemethanol, alpha-(aminomethyl)-, Ethylamine, beta-hydroxy-beta-phenyl-, .beta.-Hydroxy-.beta.-phenylethylamine, (+-)-alpha-(Aminomethyl)benzenemethanol, Ethylamine, .beta.-hydroxy-.beta.-phenyl-, dl-1-Phenyl-1-oxy-2-amino-aethan [German], CHEBI:16343, Benzyl alcohol, alpha-(aminomethyl)-, (+-)-, ULSIYEODSMZIPX-UHFFFAOYSA-N, EINECS 231-469-1, SBB063224, BRN 0971222, Benzyl alcohol, .alpha.-(aminomethyl)-, WLN: Z1YQR, Benzenemethanol, alpha-(aminomethyl)- (VAN) (9CI), Benzyl alcohol, alpha-(aminomethyl)- (VAN) (8CI), Benzenemethanol, .alpha.-(aminomethyl)- (VA, (1S)-(+)-2-Amino-1-phenylethan-1-ol, (S)-(+)-2-AMINO-1-PHENYLETHANOL, b-Hydroxyphenethylamine, 2amino-1-phenylethanol, ACMC-209ozl, AC1L1AIB, 4561-43-7, 2-amino-1-phenyl ethanol, beta-hydroxy-Phenethylamine, bmse000307, AC1Q53OG, beta-hydroxy-phenethyl-amine, SCHEMBL2021, 2-Amino-1-phenylethanol-1, dl-2-Amino-1-phenylethanol, Oprea1_790333, 2-hydroxy-2-phenylethanamine, A72405_ALDRICH, (.+/-.)-Phenylethanolamine, CHEMBL19216, 2-hydroxy-2-phenyl ethanamine, 2-hydroxy-2-phenyl-ethylamine, 09190_FLUKA, CTK3J7852, HMDB01065, alpha-(aminomethyl)benzenemethanol, BEA-0-0, NSC5021, MolPort-001-770-902, (+/-)-2-amino-1-phenylethanol, alpha-(aminomethyl)-benzyl alcohol, DL-beta-HYDROXYPHENETHYLAMINE, (2-hydroxy-2-phenyl-ethyl)-amine, beta-hydroxy-beta-phenyl-Ethylamine, CS-B0721, NSC-5021, NSC46837, 2-AMINO-1-PHENYLETHANOL HCL, dl-1-Phenyl-1-oxy-2-amino-aethan, ANW-36655, dl-beta-Phenyl-beta-hydroxyethylamine, KM1707, NSC-46837, RW1867, STK399775, 2-Amino-1-phenyl-ethanol 1HCl salt, AKOS003790979, MCULE-5691695805, QC-4634, RTC-062240, VC30297, AK105975, Benzenemethanol, .alpha.- (aminomethyl)-, Benzyl alcohol, .alpha.- (aminomethyl)-, BP-10077, KB-24371, KB-93541, LS-42668, LS-42669, LS-42670, (1R)-(-)-2-Amino-1-phenylethan-1-ol, dl-.beta.-Phenyl-.beta.-hydroxyethylamine, AB1007128, DB-020366, TC-062240, TX-016248, 4CH-014391, 4CH-017050, A5138, A9620, AM20060775, Benzenemethanol, alpha-(aminomethyl)- (VAN), Benzyl alcohol, alpha-(aminomethyl)- (VAN), FT-0084693, FT-0611013, ST24039840, ST45061436, C02735, 58463-EP2281563A1, 58463-EP2305682A1, 58463-EP2308879A1, 4-13-00-01801 (Beilstein Handbook Reference), I01-0914, I01-10426, 3B3-018763, 3B3-019304, 1477-64-1, 1936-63-6, 73-59-6

Removed Synonyms

2-Hydroxyphenethylamine, Hydroxyethylamine, L-Phenylglycinol, |A-phenylethanolamine, beta-Hydroxyphenylethylamine, (R)-2-Amino-1-phenylethanol, (S)-2-Amino-1-phenylethanol, NIOSH/DN5520000, NIOSH/DN5530000, CID1000, d-1-Phenyl-1-oxy-2-amino-aethan, l-1-Phenyl-1-oxy-2-amino-aethan, (+)-alpha-(Aminomethyl)benzyl alcohol, (-)-alpha-(Aminomethyl)benzyl alcohol, Benzenemethanol, alpha-(aminomethyl)-, d-, Benzenemethanol, alpha-(aminomethyl)-, l-, A1018, d-1-Phenyl-1-oxy-2-amino-aethan [German], DN55200000, DN55300000, l-1-Phenyl-1-oxy-2-amino-aethan [German], Benzyl alcohol, alpha-(aminomethyl)-, (+)-, Benzyl alcohol, alpha-(aminomethyl)-, (-)-, A-7000, C523155, 2549-14-6, 56613-81-1, |A-(Aminomethyl)benzyl alcohol; DL-|A-Hydroxyphenethylamine; Phenylethanolamine, 15995-85-4, 20989-17-7

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