Stearyl Alcohol → Octadecyl bromoacetate

HRID 2413974Notes

Reaction equation

HRID 2413974 reaction equation
[Br:1][CH2:2][C:3](Cl)=[O:4].[CH2:6]([OH:24])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].C(N(CC)CC)C>C(Cl)Cl>[Br:1][CH2:2][C:3]([O:24][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[O:4]

Participants

5

Reactant 3

HCID 8221Stearyl AlcoholHCID 8471TriethylamineHCID 89602Bromoacetyl chloride

Product 1

HCID 537046Octadecyl bromoacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Bromoacetylchloride (52.11 grams) is added dropwise into a stirred solution of 89.27 grams of octadecanol and 50 ml of triethylamine in 400 ml of methylene chloride at 25°-30° C. After stirring the reaction mixture at room temperature overnight under N2, the mixture is filtered and the filtrate is concentrated under reduced pressure. Purification by liquid chromatography affords octadecyl bromoacetate as a white solid, mp 37°-40° C.

Workup

  1. filtrationthe mixture is filtered
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. customPurification by liquid chromatography

Sources & evidence

ORD record
ord-8dfdc7f25c334ea39beb474fdf1c10b0
Source dataset
uspto-grants-1988_01
Patent number
US04720517

Reaction notes

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