Oxalyl chloride → HCID 21282942, compound

HRID 2232890Notes

Reaction equation

HRID 2232890 reaction equation
[CH:1]1([CH:7]([CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[CH2:8][C:9](O)=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(Cl)(=O)C([Cl:21])=O>ClCCl.CN(C)C=O>[CH:1]1([CH:7]([CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[CH2:8][C:9]([Cl:21])=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 12779965HCID 12779965, compound

Product 1

HCID 21282942HCID 21282942, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 3,3-dicyclohexylpropionic acid (15.2 g, 0.064 mol) in 225 ml of dichloromethane was cooled to 5° C. and treated with 6.8 ml (0.078 mol) of oxalyl chloride, followed by 10 drops of dimethylformamide. The cooling bath was removed and stirring was continued at room temperature. Gas evolution, which was vigorous initially, essentially ceased after 1 hour. After 3 hours, dichloromethane and excess oxalyl chloride were removed on a rotary evaporator. The residue was taken up in dichloromethane and the evaporation was repeated to give 16.1 g of a pale yellow oil.

Workup

  1. customThe cooling bath was removed
  2. customwas continued at room temperature
  3. waitAfter 3 hours
  4. customdichloromethane and excess oxalyl chloride were removed on a rotary evaporator
  5. customthe evaporation

Sources & evidence

ORD record
ord-1c23e962632440a2bea5f1c58b9111c3
Source dataset
uspto-grants-1988_11
Patent number
US04788010

Reaction notes

Loading…