Diazomethane → Desmethyl Ketoprofen Methyl Ester

HRID 1731179Notes

Reaction equation

HRID 1731179 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-6c0d1fd7a4d641f6a38180531518cb92
Source dataset
uspto-grants-1976_11
Patent number
US03995056

Reaction notes

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