Benzene → HCID 53776786, compound

HRID 436303Notes

Reaction equation

HRID 436303 reaction equation
[C:1]([OH:24])(=[O:23])[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][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].C(Cl)(=O)C(Cl)=O.[CH:31]1[CH:36]=[CH:35][CH:34]=CC=1>>[C:1]([O:24][CH2:34][CH:35]1[CH2:31][CH2:36]1)(=[O:23])[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][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

4

Reactant 3

HCID 241BenzeneHCID 8215Docosanoic AcidHCID 65578Oxalyl chloride

Product 1

HCID 53776786HCID 53776786, compound

Procedure

In a 500 ml. flask is stirred 3.2 g. of docosanoic acid in 250 ml. of dry benzene until most of acid dissolves. Oxalyl chloride (3.5 g.) is added and mixture stirred for 2 hours at room temperature under nitrogen. Solvent is removed in vacuo and fresh benzene added and 1.3 g. of cyclopropylmethyl alcohol. The reaction product is worked up by washing with water and brine, drying over calcium sulfate and evaporation of solvent to yield cyclopropylmethyl docosanoate m.p. 44°, which can be further purified by recrystallization from methanol.

Workup

  1. stirringmixture stirred for 2 hours at room temperature under nitrogen
  2. customSolvent is removed in vacuo and fresh benzene
  3. additionadded
  4. washby washing with water and brine
  5. dry with materialdrying over calcium sulfate and evaporation of solvent

Sources & evidence

ORD record
ord-f722cb6beda54a87ae101a47918713e3
Source dataset
uspto-grants-1977_02
Patent number
US04008258

Reaction notes

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