Benzene → Cyclopropylmethyl dodecanoate

HRID 436298Notes

Reaction equation

HRID 436298 reaction equation
[C:1]([OH:14])(=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].C(Cl)(=O)C(Cl)=O.[CH:21]1[CH:26]=[CH:25][CH:24]=CC=1>>[C:1]([O:14][CH2:24][CH:25]1[CH2:21][CH2:26]1)(=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

4

Reactant 3

HCID 241BenzeneHCID 3893Lauric AcidHCID 65578Oxalyl chloride

Product 1

HCID 21454063Cyclopropylmethyl dodecanoate

Procedure

To a stirred solution of 3.01 g. of lauric acid in benzene, under nitrogen, is added 5.8 g. of oxalyl chloride. The mixture is stirred at room temperature for 2 hours and then concentrated in vacuo at 40°. To the concentrate is added fresh benzene and 3.25 g. of cyclopropylmethyl alcohol. The solution is stirred overnight at room temperature and then diluted with water. The reaction mixture is worked up by washing with water and brine, drying over calcium sulfate, concentrating the organic phase under reduced pressure and purifying by distillation to yield cyclopropylmethyl laurate (cyclopropanemethyl-n-dodecanoate), b.p. (bath) 90° at 0.005 mm.

Workup

  1. concentrationconcentrated in vacuo at 40°
  2. additionTo the concentrate is added fresh benzene and 3.25 g
  3. stirringThe solution is stirred overnight at room temperature
  4. additiondiluted with water
  5. washby washing with water and brine
  6. dry with materialdrying over calcium sulfate
  7. concentrationconcentrating the organic phase under reduced pressure
  8. distillationpurifying by distillation

Sources & evidence

ORD record
ord-61a966504fc047c7beb4954f613b6e87
Source dataset
uspto-grants-1977_02
Patent number
US04008258

Reaction notes

Loading…