Synthesis of cinnamyl alcohol

Preparation of cinnamyl alcohol

Alternative Names: Cinnamic alcohol; 3-phenylprop-2-en-1-ol; 3-phenyl-2-propen-1-ol; Zimtalcohol;

Preparation of cinnamyl alcohol

Preparation of cinnamyl alcohol

21.7 g of freshly distilled cinnamaldehyde are added to a suspension of 40 g of sodium trimethoxyborohydride in 100 ml of ether. During the addition the mixture begins to boil. When all cinnamaldehyde has been added the obtained mixture is heated for 4 hours, under reflux, then the vessel is cooled and dilute sulfuric acid is added until evolution of hydrogen ceases. The ethereal solution is dried over sodium sulfate and the solvent is evaporated in vacuum. Fractional distillation yields 80% (17.5 g) of cinnamyl alcohol, b.p. 134-135°/13 mm.

E. Schenker, Angew. Chem., 73, 81 (1961).

IUPAC Name

(E)-3-phenylprop-2-en-1-ol

InChI

InChI=1S/C9H10O/c10-8-4-7-9-5-2-1-3-6-9/h1-7,10H,8H2/b7-4+

InChI Key

OOCCDEMITAIZTP-QPJJXVBHSA-N

Canonical SMILES

C1=CC=C(C=C1)C=CCO

Isomeric SMILES

C1=CC=C(C=C1)/C=C/CO

MeSH Synonyms

3-phenyl-2-propene-1-ol, 3-phenylprop-2-en-1-ol, cinnamic alcohol, cinnamyl alcohol, cinnamyl alcohol, (E)-isomer, cinnamyl alcohol, titanium (4+) salt

Depositor-Supplied Synonyms

cinnamyl alcohol, cinnamic alcohol, 3-phenylprop-2-en-1-ol, 104-54-1, 3-PHENYL-2-PROPEN-1-OL, Zimtalcohol, Styryl carbinol, 3-Phenylallyl alcohol, Styrone, Styryl alcohol, 3-Phenyl-2-propenol, (E)-3-phenylprop-2-en-1-ol, trans-cinnamyl alcohol, (E)-cinnamyl alcohol, Styrylcarbinol, Phenyl-2-propen-1-ol, (E)-3-Phenyl-2-propen-1-ol, (2E)-3-phenylprop-2-en-1-ol, FEMA No. 2294, CHEBI:33227, gamma-Phenylallyl alcohol, 4407-36-7, Alkohol skoricovy [Czech], Cinnamic alcohol (natural), UNII-SS8YOP444F, 1-Phenylprop-1-en-3-ol, 2-Propen-1-ol, 3-phenyl-, 2-Propen-y1-ol, 3-phenyl-, CCRIS 3191, CHEMBL324794, HSDB 5011, (E)-3-phenyl-prop-2-en-1-ol, OOCCDEMITAIZTP-QPJJXVBHSA-N, 3-Fenyl-2-propen-1-ol [Czech], NSC 8775, EINECS 203-212-3, 2-Propen-1-ol, 3-phenyl-, (E)-, Propenoic acid, 3-phenyl-, (trans)-, BRN 1903999, AI3-00949, Alkohol skoricovy, Phenylallyl alcohol, 3-Fenyl-2-propen-1-ol, .gamma.-Phenylallyl alcohol, CHEBI:17177, Chnnamyl alcohol, NCGC00166097-01, (E)-Cinnam Alcohol, AC1NSTME, AC1Q1HEH, HYDROXYMETHYLSTYRENE, bmse010256, Epitope ID:150920, AC1Q77UL, AC1Q77UM, SS8YOP444F, WLN: Q2U1R, SCHEMBL39219, W229407_ALDRICH, 108197_ALDRICH, Jsp000446, 96330_FLUKA, NSC8775, MolPort-001-783-093, MolPort-005-273-806, BB_NC-2246, NSC-8775, AR-1F5049, BBL027413, BDBM50310446, NSC623440, SBB058645, STL146348, ZINC01529427, AKOS005265255, EBD2197996, LS-2357, NE10243, NSC-623440, RP17318, RTR-033383, 4CN-1216, AJ-26595, AK104332, AN-24683, CJ-23893, I792, KB-76100, KB-77822, AB1003816, KB-236832, KB-288227, TR-033383, FT-0623834, N1483, ST24022977, ST51036393, W2111, EN300-19335, C02394, (E)-3-phenyl-2-propen-1-ol(E)-cinnamyl alcohol, 1-06-00-00281 (Beilstein Handbook Reference), A800999, I14-60909, 3B1-005357, InChI=1/C9H10O/c10-8-4-7-9-5-2-1-3-6-9/h1-7,10H,8H2/b7-4, 30584-69-1

Removed Synonyms

3-phenyl-2-propene-1-ol, cinnamyl alcohol, (E)-isomer, c0362, cinnamyl alcohol, titanium (4+) salt, CID5315892, C020722, 10508-00-6, 6006-80-0

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