Water → 5-Keto Vioxx

HRID 1458319Notes

Reaction equation

HRID 1458319 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([OH:14])=[O:13])=[CH:7][CH:6]=1)(=[O:4])=[O:3].C(O[C:18](=O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=O.[K].O.C[C:29](OC(C)=O)=[O:30]>>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[C:12]([O:14][C:29](=[O:30])[C:18]=2[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[O:13])=[CH:9][CH:10]=1)(=[O:3])=[O:4]

Participants

5

Reactant 4

HCID 962WaterHCID 7918Acetic Anhydride2×HCID 5723454-Mesylphenylacetic acidHCID 86753446HCID 86753446, compound

Product 1

HCID 121856695-Keto Vioxx

Procedure

A mixture of 21.4 g (0.10 mol) of 4-(methylsulfonyl) phenylacetic acid [Forrest, et al., J. Chem. Soc. (1948), 1501-1506] and 18.8 g (0.10 mol) of potassium benzoyl formate in 200 mL of Ac2O is stirred and refluxed for 2 h. The reaction mixture is cooled to r.t. and poured into 1L of H2O and stirred until the Ac2O dissolves (ca. 2h). The precipitate is filtered and dried to obtain the title compound. If desired, it is recrystallized from HOAc or acetone.

Workup

  1. temperaturerefluxed for 2 h
  2. filtrationThe precipitate is filtered
  3. customdried

Sources & evidence

ORD record
ord-892bcb193de04e209fda8d95492084d6
Source dataset
uspto-grants-1998_12
Patent number
US05849943

Reaction notes

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