Chloroacetyl chloride → Erucyl 2-chloroacetate

HRID 645331Notes

Reaction equation

HRID 645331 reaction equation
[CH2:1]([OH:23])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]/[CH:13]=[CH:14]\[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].[Cl:24][CH2:25][C:26](Cl)=[O:27]>C1(C)C=CC=CC=1>[Cl:24][CH2:25][C:26]([O:23][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]/[CH:13]=[CH:14]\[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[O:27]

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 5354168Erucyl alcohol

Product 1

HCID 86592452Erucyl 2-chloroacetateYield 95.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

To erucyl alcohol (2) (101.5 g, 310.8 mmol) in 200 ml of toluene was added chloroacetyl chloride (38.6 g, 341.9 mmol). The reaction mixture was stirred at 25° C. for 3 hours. The reaction mixture was then washed with water (100 ml) and the aqueous and organic layers separated The organic layer was dried over sodium sulphate and the solvent removed in vacuo to yield erucyl 2-chloroacetate (3) (118.7 g, 94.3%).

Workup

  1. washThe reaction mixture was then washed with water (100 ml)
  2. customthe aqueous and organic layers separated The organic layer
  3. dry with materialwas dried over sodium sulphate
  4. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-7b30aa53a0474628aca9db145768a82c
Source dataset
uspto-grants-2010_04
Patent number
US07704926B2

Reaction notes

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