Benzene → HCID 86734498, compound

HRID 436302Notes

Reaction equation

HRID 436302 reaction equation
[C:1]([OH:20])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].C(Cl)(=O)C(Cl)=O.[CH:27]1[CH:32]=[CH:31][CH:30]=CC=1>>[CH:32]1([CH2:27][CH:2]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]=[CH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:1]([OH:20])=[O:19])[CH2:30][CH2:31]1.[C:1]([OH:20])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

4

Reactant 3

HCID 241BenzeneHCID 65578Oxalyl chlorideHCID 445639Oleic Acid

Product 1

HCID 86734498HCID 86734498, compound

Procedure

Oleic acid (1.8 g.) is dissolved in about 100 ml. of dry benzene and 2.4 g. of oxalyl chloride is added with stirring, under nitrogen, at room temperature. After 2 hours, solvent is removed under reduced pressure in 30° water bath. Fresh dry benzene (100 ml.) is added and 9.4 g. of cyclopropylmethyl alcohol. The reaction mixture is stirred overnight at room temperature. The reaction is worked up by washing with water and brine, drying over calcium sulfate and evaporation of solvent to yield the cyclopropylmethyl ester of oleic acid (cyclopropylmethyloctadec-9-enoate) b.p. 120° (bath) at 0.01 mm., which can be further purified by distillation.

Workup

  1. customsolvent is removed under reduced pressure in 30° water bath
  2. additionFresh dry benzene (100 ml.) is added
  3. stirringThe reaction mixture is stirred overnight at room temperature
  4. washby washing with water and brine
  5. dry with materialdrying over calcium sulfate and evaporation of solvent

Sources & evidence

ORD record
ord-acb9ceffc3a84194a78883c507dacdc1
Source dataset
uspto-grants-1977_02
Patent number
US04008258

Reaction notes

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