Chloroacetyl chloride → HCID 86755078, compound

HRID 849982Notes

Reaction equation

HRID 849982 reaction equation
[CH2:1]([OH:19])[CH2:2][CH2:3][CH2:4][CH2:5]/[CH:6]=[CH:7]\[CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].C(N(CC)CC)C.[Cl:27][CH2:28][C:29](Cl)=[O:30]>C(Cl)Cl>[CH2:1]([O:19][C:29](=[O:30])[CH2:28][Cl:27])[CH2:2][CH2:3][CH2:4][CH2:5]/[CH:6]=[CH:7]\[CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 9795274gamma-Linolenyl alcohol

Product 1

HCID 86755078HCID 86755078, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To an ice-cooled solution of z,z,z-octadeca-6,9,12-trienol (2 g, 7.56 mmol) and triethylamine (2.02 g, 20 mmol) in methylene chloride (20 ml) was added dropwise with stirring chloroacetyl chloride (1.13 g, 10 mmol) in methylene chloride (20 ml) under an atmosphere of nitrogen. On completion of the reaction as shown by tlc, the mixture was washed with water (2×100 ml) and saturated sodium chloride solution (100 ml). The organic phase was dried with magnesium sulfate, filtered and concentrated under reduced pressure. Toluene (100 ml) was added to azeotropically remove final traces of water. z,z,z-octadeca-6,9,12-trienyl-(2-chloro)acetate was obtained as a dark brown oil.

Workup

  1. customOn completion of the reaction
  2. washthe mixture was washed with water (2×100 ml) and saturated sodium chloride solution (100 ml)
  3. dry with materialThe organic phase was dried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. additionToluene (100 ml) was added
  7. customto azeotropically remove final traces of water

Sources & evidence

ORD record
ord-46973a7e6516416a9794122231544b6b
Source dataset
uspto-grants-2000_01
Patent number
US06015821

Reaction notes

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