Chloroacetic Acid → 3,7-dimethyloct-6-en-1-yl chloroacetate

HRID 1765958Notes

Reaction equation

HRID 1765958 reaction equation
[Cl:1][CH2:2][C:3]([OH:5])=[O:4].[CH3:6][CH:7]([CH2:11][CH2:12][CH:13]=[C:14]([CH3:16])[CH3:15])[CH2:8][CH2:9]O>[OH-].[K+].O>[CH2:9]([O:4][C:3](=[O:5])[CH2:2][Cl:1])[CH2:8][CH:7]([CH2:11][CH2:12][CH:13]=[C:14]([CH3:16])[CH3:15])[CH3:6]

Participants

5

Reactant 2

HCID 300Chloroacetic AcidHCID 8842Citronellol2×

Product 1

HCID 2310313,7-dimethyloct-6-en-1-yl chloroacetateYield 85.1%

Reagents, catalysts & solvents 2

HCID 14797Potassium HydroxideCatalystHCID 962WaterSolvent

Procedure

A mixture of 94.5 g (1.0 mol) of monochloroacetic acid and 203.2 g (1.4 mol) of 3,7-dimethyl-6-octen-1-ol (citronellol) was heated for 6 h at 50 mbar to 130° C., wherein the water formed by esterification was distilled off via a column. The reaction mixture obtained had an acid value of 5 mg KOH/g. Unreacted citronellol was then distilled off at 6 mbar and a bottoms temperature of up to 130° C. Distillation of the residue at 6 mbar yielded 198 g of chloroacetic acid citronellyl ester as a colourless liquid.

Workup

  1. customformed by esterification
  2. distillationwas distilled off via a column
  3. customThe reaction mixture obtained
  4. distillationwas then distilled off at 6 mbar
  5. customup to 130° C
  6. distillationDistillation of the residue at 6 mbar

Sources & evidence

ORD record
ord-ffc27537c5f74f5487be0f16c623ed3b
Source dataset
uspto-grants-2007_06
Patent number
US07229958B2

Reaction notes

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