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

HRID 248165Notes

Reaction equation

HRID 248165 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].CN(C1C=CC=CN=1)C.Br[CH2:28][C:29](=[CH2:35])[C:30]([O:32][CH2:33][CH3:34])=[O:31]>C(Cl)Cl>[CH2:1]([O:17][CH2:35][C:29](=[CH2:28])[C:30]([O:32][CH2:33][CH3:34])=[O:31])[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 3106202-(Bromomethyl)acrylic acid ethyl ester

Product 1

HCID 12971817Ethyl 2-[(hexadecyloxy)methyl]-2-propenoateYield 261.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1.9 g of hexadecanol in 40 ml of methylene chloride containing 700 mg of dimethylaminopyridine is added 500 mg of ethyl 2-bromomethyl-2-propenoate followed by continued stirring for 18 hours. The solvent is evaporated to give 2.4 g of the desired product.

Workup

  1. customThe solvent is evaporated

Sources & evidence

ORD record
ord-a809b9129d0249679d8a3637c3af828d
Source dataset
uspto-grants-1993_05
Patent number
US05208223

Reaction notes

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