Cetyl Alcohol → Ethyl 2-[(hexadecyloxy)methyl]-2-propenoate

HRID 248138Notes

Reaction equation

HRID 248138 reaction equation
[CH2:1]([OH:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].C(O[CH2:22][C:23](=[CH2:29])[C:24]([O:26][CH2:27][CH3:28])=[O:25])(=O)C.CN(C1C=CC=CN=1)C>ClCCl>[CH2:1]([O:17][CH2:29][C:23](=[CH2:22])[C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 2682Cetyl AlcoholHCID 218852-DimethylaminopyridineHCID 10997496Ethyl 2-(acetoxymethyl)acrylate

Product 1

HCID 12971817Ethyl 2-[(hexadecyloxy)methyl]-2-propenoateYield 39.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 1.1 g of 1-hexadecanol and 400 mg of 2-[(acetyloxy)methyl]-2-propenoic acid, ethyl ester in 15 ml of dichloromethane is added 550 mg of dimethylaminopyridine. This mixture is stirred overnight, then the solvent is evaporated and the residue subjected to preparative tlc (25% ethyl acetate/petroleum ether), to give 324 mg of the desired compound.

Workup

  1. customthe solvent is evaporated

Sources & evidence

ORD record
ord-a68765fbb5c5487ea982e6d8ac4db2f2
Source dataset
uspto-grants-1993_05
Patent number
US05208223

Reaction notes

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