Methanol → Methyl 6,8-dichlorooctanoate

HRID 983659Notes

Reaction equation

HRID 983659 reaction equation
[Cl:1][CH:2]([CH2:10][CH2:11][Cl:12])[CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8].[CH3:13]O>Cl>[Cl:1][CH:2]([CH2:10][CH2:11][Cl:12])[CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O:9][CH3:13])=[O:8]

Participants

4

Reactant 2

HCID 887MethanolHCID 99644476,8-dichlorooctanoic Acid

Product 1

HCID 22445991Methyl 6,8-dichlorooctanoateYield 98.6%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

9 g (0.042 moles) of (+)-6,8-dichlorooctanoic acid are dissolved in 120 ml of methanol containing 0.45 ml of aqueous hydrochloric acid at 37% by weight. The solution is refluxed for two hours, the solvent is evaporated at reduced pressure, 17 ml of toluene are added and the obtained solution is washed twice with 10 ml of water. The toluene phase is concentrated under vacuum, thus obtaining 9.4 g of methyl (+)-6,8-dichlorooctanoate (yield=98.6%).

Workup

  1. temperatureThe solution is refluxed for two hours
  2. customthe solvent is evaporated at reduced pressure, 17 ml of toluene
  3. additionare added
  4. washthe obtained solution is washed twice with 10 ml of water
  5. concentrationThe toluene phase is concentrated under vacuum

Sources & evidence

ORD record
ord-0e53d33d585d42df9024bba873868f79
Source dataset
uspto-grants-2005_03
Patent number
US06864374B2

Reaction notes

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