Synthesis of 1-phenylethanol (alpha-methylbenzyl alcohol)

Preparation of 1-phenylethanol

6 g of clean magnesium ribbon or filings are placed in a 1 liter dry, round flask connected with a long reflux condenser and dropping funnel. A mixture of 36 g of methyl iodide and 50 ml of ether, previously well dried over sodium is prepared and 20 ml of this mixture poured on to the magnesium. In a few seconds a vigorous reaction usually sets in or, if it is delayed, may be started by adding a crystal of iodine. When the first reaction has subsided, 70 ml of dry ether added and run in the remainder of the methyl iodide and ether mixture drop by drop from a dropping funnel. The reaction mixture is then boiled for a short time until the magnesium is dissolved. When the magnesium is dissolved the flask is immersed in ice-water, and 26 g of benzaldehyde are added mixed with an equal volume of dry ether from the dropping-funnel, with constant stirring. The solid magnesium compound starts to separate and the reaction is left over-night. The next day the reaction flask is cooled in ice-water and sufficient dilute sulfuric or hydrochloric acid added drop by drop. The aqueous layer is removed in a separating-funnel and wash the ether, first with sodium carbonate solution, then with sodium bisulfite (to remove free iodine) and again with sodium carbonate. Ether extract is dried over potassium carbonate and ether is removed by evaporation. The 1-phenylethanol is distilled under reduced pressure 100° C at 15 mm. ; 110-111° C at 28 mm. ; 118° C at 40 mm. The yield of 1-phenylethanol is 20 grams.

A Class-Book of Organic Chemistry, by J. B. Cohen, 12, 1919

Preparation of 1-phenylethanol

Preparation of 1-phenylethanol

15 g of acetophenone are dissolved in 150 g of absolute alcohol, and the whole warmed on a water bath. 15 g of sodium wire are rapidly added, and when reaction has ceased, carbon dioxide is passed in until it is no longer absorbed. 350 ml of water are added and the mixture evaporated on a water bath until nothing further distils, the alcohol being recovered. The residue is extracted with ether and dried over potassium carbonate, the ether removed on a water bath, and the residue fractionated under reduced pressure, the fraction 97-103 ° at 15 mm. being retained. Yield 45%. Colourless liquid; slightly soluble in water. b.p. 198° C/760 mm; b.p. 118° C/40 mm; b.p. 111° C/20 mm; b.p. 100° C/15 mm.

Systematic organic chemistry, by W. M. Cumming, 186, 1937.

IUPAC Name

1-phenylethanol

InChI

InChI=1S/C8H10O/c1-7(9)8-5-3-2-4-6-8/h2-7,9H,1H3

InChI Key

WAPNOHKVXSQRPX-UHFFFAOYSA-N

Canonical SMILES

CC(C1=CC=CC=C1)O

MeSH Synonyms

1-phenylethanol, alpha-hydroxyethylbenzene, alpha-methylbenzyl alcohol, methylphenyl carbinol

Depositor-Supplied Synonyms

1-Phenylethanol, 98-85-1, ALPHA-METHYLBENZYL ALCOHOL, Methylphenyl carbinol, Styrallyl alcohol, Methylphenylcarbinol, 1-Phenethyl alcohol, Styralyl alcohol, 1-Phenylethan-1-ol, 1-Phenylethyl alcohol, (1-Hydroxyethyl)benzene, Phenylmethylcarbinol, Ethanol, 1-phenyl-, Methanol, methylphenyl-, alpha-Phenylethyl alcohol, alpha-Phenylethanol, 1-Phenyl-1-hydroxyethane, Benzenemethanol, .alpha.-methyl-, sec-Phenethyl alcohol, 1-Fenylethanol, alpha-Methylbenzenemethanol, NCI-C55685, (+/-)-1-Phenylethanol, Fenyl-methylkarbinol, .alpha.-Phenylethanol, Methyl phenyl carbinol, Benzyl alcohol, .alpha.-methyl-, 1-Fenylethanol [Czech], alpha-Methyl-benzmethanol, FEMA Number 2685, 1-PHENYL-ETHANOL, NSC 25502, .alpha.-Phenethyl alcohol, .alpha.-Phenylethyl alcohol, .alpha.-Methylbenzyl alcohol, .alpha.-Methylbenzenemethanol, Fenyl-methylkarbinol [Czech], CHEBI:669, Styrene alcohol, Benzenemethanol, alpha-methyl-, Benzyl alcohol, alpha-methyl-, FEMA No. 2685, CCRIS 2367, (+/-)-1-Phenylethyl Alcohol, (1)-alpha-Methylbenzyl alcohol, HSDB 4164, WAPNOHKVXSQRPX-UHFFFAOYSA-N, (+/-)-alpha-Methylbenzyl alcohol, EINECS 202-707-1, EINECS 236-361-8, SBB058702, UN2937, beta-Phenethyl alcohol, alpha-Phenethyl alcohol, AI3-02936, 1-Phenyl ethyl alcohol, 13323-81-4, DL-sec-Phenethyl alcohol, (S)-1-Phenylethyl alcohol, (S)-(-)-sec-Phenethyl Alcohol, 1-phenyl ethanol, Benzenemethanol, alpha-methyl-, (R)-, methylbenzyl alcohol, Benzenemethanol, .alpha.-methyl-, (R)-, Benzenemethanol, .alpha.-methyl-, (S)-, beta-Phenethylalcohol, 1-hydroxyethylbenzene, 1-phenyl-1-ethanol, 1-phenylethane-1-ol, a-methylbenzyl alcohol, methyl phenyl methanol, DL-1-Phenethylalcohol, m ethyl phenyl methanol, (+) alpha-phenylethanol, AC1Q1QWS, AC1Q2BTJ, (+)-Methylphenylcarbinol, 1-Phenyl-1-ethylalcohol, DSSTox_CID_859, ACMC-1BP1S, ACMC-209ct5, ACMC-209d6x, .alpha.-Hydroxyethylbenzene, alpha-methyl-benzenemethanol, alpha-Methyl-benzyl alcohol, AC1L1OP4, Benzenemethanol, ?-methyl-, SCHEMBL2164, DSSTox_RID_75830, DSSTox_GSID_20859, P13800_ALDRICH, KSC180A0N, W268518_ALDRICH, (+/-)-sec-Phenethyl Alcohol, CHEMBL508917, WLN: QY1 & R, dl-.alpha.-Methylbenzyl alcohol, 09449_FLUKA, 77850_FLUKA, CTK0I0006, DL-alpha-METHYLPHENYLCARBINOL, MolPort-001-788-492, LS-24, NSC25502, Tox21_200505, ANW-40962, AR-1C5314, NSC-25502, AKOS000121326, AKOS016038258, Benzenemethanol, alpha-methyl-, (S)-, MCULE-1985443213, RTR-005646, RTR-033037, UN 2937, CAS-98-85-1, (R)-(+)-sec-PHENYLETHYL ALCOHOL, NCGC00248663-01, NCGC00258059-01, AK-58033, AN-24496, AN-49209, AN-49366, KB-47293, SC-01127, SC-01292, Benzenemethanol, alpha-methyl-, (alphaS)-, DB-043114, TR-005646, FT-0613332, FT-0633624, M0163, ST24038180, alpha-Methylbenzyl alcohol [UN2937] [Poison], C07112, 16568-EP2281563A1, 16568-EP2298744A2, 16568-EP2301918A1, 16568-EP2308857A1, 16568-EP2316459A1, alpha-Methylbenzyl alcohol [UN2937] [Poison], I01-7503, I14-7357, 3B3-024407

Removed Synonyms

Phenylethanol, Phenyl Ethanol, Ethanol, phenyl-, (S)-1-Phenylethanol, beta-Hydroxyethylbenzene, (R)-(+)-1-Phenylethanol, (S)-(-)-1-Phenylethanol, UNII-E6O895DQ52, (R)-alpha-Methylbenzyl alcohol, CID7409, (R)-(+)-1-Phenylethyl Alcohol, (S)-(-)-1-Phenylethyl Alcohol, 1-ethylcyclohexa-2,4-dien-1-ol, (S)-(-)-Sec-Phenylethyl alcohol, 1517-69-7, 1445-91-6, 1321-27-3, 6291-04-9

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