Synthesis of trans crotyl alcohol

Preparation of trans-crotyl alcohol

Alternative Names: 2-buten-1-ol; 2-butenol; 3-methylallyl alcohol; 2-butenyl alcohol

Preparation of trans-crotyl alcohol (2-buten-1-ol; 2-butenol; 3-methylallyl alcohol; 2-butenyl alcohol)

Preparation of trans-crotyl alcohol (2-buten-1-ol; 2-butenol; 3-methylallyl alcohol; 2-butenyl alcohol)

2 g of lithium aluminum hydride are dissolved in 150 ml of anhydrous ether. This solution is dropwise added during 30-60 minutes period into a stirred solution of 3 g 2-butyn-1-ol in 25 ml of anhydrous ether. When the addition is complete the obtained mixture is boiled under reflux for a further 3 hours. After cooling, the excess of lithium aluminum hydride is decomposed with 14 ml of ethyl acetate and 24 ml of saturated ammonium chloride solution. The mixture is then filtered and the ethereal layer is washed with water and dried with the mixture of sodium sulfate and potassium carbonate. After removal of the ether the residue is distilled in a vacuum, yielding 1.6 g of trans-crotyl alcohol (b.p. 122° C; nD=1.4278).

K. R. Bharucha and B. C. L. Weedon, J. Chem. Soc, 1953, 1584.

IUPAC Name

(E)-but-2-en-1-ol

InChI

InChI=1S/C4H8O/c1-2-3-4-5/h2-3,5H,4H2,1H3/b3-2+

InChI Key

WCASXYBKJHWFMY-NSCUHMNNSA-N

Canonical SMILES

CC=CCO

Isomeric SMILES

C/C=C/CO

MeSH Synonyms

crotonol, crotonyl alcohol, crotonyl alcohol, (cis)-isomer, crotonyl alcohol, (trans)-isomer, crotyl alcohol

Depositor-Supplied Synonyms

Crotonyl alcohol, 2-Buten-1-ol, Crotyl alcohol, 2-Butenol, 3-Methylallyl alcohol, 2-Butenyl alcohol, 2-BUTENE-1-OL, Krotylalkohol, (E)-But-2-en-1-ol, (2E)-but-2-en-1-ol, 2-Buten-1-ol, (E)-, 2-Buten-1-ol, (2E)-, Krotylalkohol [Czech], Crotyl alcohol (VAN), 6117-91-5, Crotonyl alcohol (VAN), NSC 17480, UNII-L585TY5908, WCASXYBKJHWFMY-NSCUHMNNSA-N, EINECS 228-086-7, 1-Hydroxy-2-butene, BRN 1719374, 2-Buten-1-o1, AI3-14902, CH3CH=CHCH2OH, 504-61-0, crotonol, trans-2-Buten-1-Ol, WCASXYBKJHWFMY-UHFFFAOYSA-N, Propenylcarbinol, E-crotyl alcohol, Crotyl alcohol, mixture of cis and trans, 1-Hydroxybut-2-ene, trans-Crotonyl Alcohol, PubChem21075, (E)-2-Buten-1-ol, AC1LCV98, C86006_ALDRICH, InChI=1/C4H8O/c1-2-3-4-5/h2-3,5H,4H2,1H3/b3-2, CHEMBL118459, 28091_FLUKA, CHEBI:62891, MolPort-001-759-965, BB_NC-2275, EINECS 207-996-8, 7256AF, BBL027414, STL372963, ZINC01758744, AKOS009157989, L585TY5908, RP18314, AN-21444, KB-76196, LS-47229, SC-69597, B0696, FT-0611624, FT-0628372, 2-01-00-00480 (Beilstein Handbook Reference), T7100762, UNII-D7F26UNN0B component WCASXYBKJHWFMY-NSCUHMNNSA-N, 542-72-3

Removed Synonyms

but-2-en-1-ol, UNII-D7F26UNN0B, crotonyl alcohol, (cis)-isomer, crotonyl alcohol, (trans)-isomer, CID637922, C007153

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