Diazomethane → Desmethyl Ketoprofen Methyl Ester

HRID 1579777Notes

Reaction equation

HRID 1579777 reaction equation
[N+](=[CH2:3])=[N-].[C:4]([C:12]1[CH:13]=[C:14]([CH2:18][C:19]([OH:21])=[O:20])[CH:15]=[CH:16][CH:17]=1)(=[O:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>C(Cl)Cl>[C:4]([C:12]1[CH:13]=[C:14]([CH2:18][C:19]([O:21][CH3:3])=[O:20])[CH:15]=[CH:16][CH:17]=1)(=[O:11])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 30931(3-Benzoylphenyl)acetic acid

Product 1

HCID 10634678Desmethyl Ketoprofen Methyl Ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1300 ml of a methylene chloride solution titrating 12.5 g/liter of diazomethane was added progressively at 10°-15°C to a solution of 50 g of m-benzoyl-phenyl acetic acid in 500 ml of methylene chloride and after stirring for 15 minutes, excess diazomethane was destroyed by the addition of acetic acid. The organic solution was washed with an aqueous saturated sodium bicarbonate solution and then with water and evaporated to dryness under reduced pressure to obtain 52.5 g of methyl m-benzoyl-phenyl-acetate which was used as is for the α-alkylation step.

Workup

  1. customexcess diazomethane was destroyed by the addition of acetic acid
  2. washThe organic solution was washed with an aqueous saturated sodium bicarbonate solution
  3. customwith water and evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-a95d54c2308e4305963d50fef165108e
Source dataset
uspto-grants-1976_01
Patent number
US03931302

Reaction notes

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