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

HRID 1885447Notes

Reaction equation

HRID 1885447 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-f8e549078c95486f848730e4aa62ebd7
Source dataset
uspto-grants-1992_09
Patent number
US05144045

Reaction notes

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