Ethyl Acrylate → Ethyl 3-(hexadecylthio)propanoate

HRID 248169Notes

Reaction equation

HRID 248169 reaction equation
[CH2:1]([SH: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:18]([O:22][CH2:23][CH3:24])(=[O:21])[CH:19]=[CH2:20]>C(N(CC)CC)C>[CH2:1]([S:17][CH2:20][CH2:19][C:18]([O:22][CH2:23][CH3:24])=[O:21])[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

4

Reactant 2

HCID 8821Ethyl AcrylateHCID 18015Hexadecanethiol

Product 1

HCID 19764352Ethyl 3-(hexadecylthio)propanoateYield 184.3%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A solution of 15 g of hexadecylmercaptan, 3.0 g of ethyl acrylate and 2 ml of triethylamine is stirred at ambient temperature for 18 hours. The solvent is evaporated and the concentrate purified by high pressure liquid chromatography, to give 19.8 g of the desired product.

Workup

  1. customThe solvent is evaporated
  2. customthe concentrate purified by high pressure liquid chromatography

Sources & evidence

ORD record
ord-46a26e1746954432a89f22281af2d4ff
Source dataset
uspto-grants-1993_05
Patent number
US05208223

Reaction notes

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