monoMethyl adipate → Methyl 6-chloro-6-oxohexanoate

HRID 2357750Notes

Reaction equation

HRID 2357750 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].[CH3:7][O:8][C:9](=[O:17])[CH2:10][CH2:11][CH2:12]CC(O)=O>ClCCl>[CH3:7][O:8][C:9](=[O:17])[CH2:10][CH2:11][CH2:12][CH2:1][C:2]([Cl:4])=[O:3]

Participants

4

Reactant 2

HCID 12328monoMethyl adipateHCID 65578Oxalyl chloride

Product 1

HCID 520737Methyl 6-chloro-6-oxohexanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of oxalyl chloride (0.040 mole) in dichloromethane (20 mL) is added dropwise to an ice bath cooled solution of adipic acid monomethyl ester (Aldrich) (0.040 mole) in dichloromethane (50 mL). The reaction is stirred at ambient temperature for 5 hours. The reaction solution is washed with 5% aqueous sodium bicarbonate, with water, and then with a saturated sodium chloride solution. The organic layer may be dried over sodium sulfate, filtered and concentrated in vacuo to give 6-methoxy-6-oxohexanoyl chloride. See Musso, et. al., J. Med. Chem., (2003) 46:409.

Workup

  1. washThe reaction solution is washed with 5% aqueous sodium bicarbonate, with water
  2. dry with materialThe organic layer may be dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b4a04ad364414c4f8fc27b1a581841ee
Source dataset
uspto-grants-2010_07
Patent number
US07763612B2

Reaction notes

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