Oxalyl chloride → Ethyl 7-(4-chlorophenyl)-7-oxoheptanoate

HRID 567160Notes

Reaction equation

HRID 567160 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([OH:12])=O)[CH3:2].[C:14]([Cl:19])(=O)[C:15](Cl)=O>CN(C)C=O.O1CCCC1>[Cl:19][C:14]1[CH:15]=[CH:7][C:6]([C:10]([CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:13])=[O:12])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 118383Ethyl hydrogen heptane-1,7-dioate

Product 1

HCID 11065929Ethyl 7-(4-chlorophenyl)-7-oxoheptanoateYield 196.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

N,N-dimethylformamide(1 drop) was added to a tetrahydrofuran solution(40 ml) of pimelic acid monoethyl ester(25.5 g), and thereto oxalyl chloride(18.8 g) was added dropwise. After stirring for 2 hours at room temperature, the reaction mixture was concentrated. The residue was added dropwise to a mixture of chlorobenzene(61.0 g) and aluminum chloride anhydrous (36.1 g) under ice water. After stirring for 3 hours, the reaction mixture was poured into 1N-hydrochloric acid, and extracted with ethyl acetate. The ethyl acetate layer was washed with water, and dried(MgSO4). The solvent was evaporated to give ethyl 6-(4-chlorobenzoyl)hexanate (37.7 g, 97%) as an oily substance.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. additionThe residue was added dropwise to a mixture of chlorobenzene(61.0 g) and aluminum chloride anhydrous (36.1 g) under ice water
  3. stirringAfter stirring for 3 hours
  4. additionthe reaction mixture was poured into 1N-hydrochloric acid
  5. extractionextracted with ethyl acetate
  6. washThe ethyl acetate layer was washed with water, and dried(MgSO4)
  7. customThe solvent was evaporated

Sources & evidence

ORD record
ord-8e032c037879423db8794974e07bf39a
Source dataset
uspto-grants-2001_01
Patent number
US06177452B1

Reaction notes

Loading…