p-Toluenesulfonic acid → 6-Acetoxy-2-naphthyl-alpha-methylacetic acid

HRID 1973996Notes

Reaction equation

HRID 1973996 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([CH:12]([CH3:16])[C:13]([OH:15])=[O:14])[CH:6]=[CH:5]2.[C:17](OC(=O)C)(=[O:19])[CH3:18].C1(C)C=CC(S(O)(=O)=O)=CC=1>>[C:17]([O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([CH:12]([CH3:16])[C:13]([OH:15])=[O:14])[CH:6]=[CH:5]2)(=[O:19])[CH3:18]

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7918Acetic AnhydrideHCID 162920Desmethylnaproxen

Product 1

HCID 203351926-Acetoxy-2-naphthyl-alpha-methylacetic acid

Procedure

A mixture of 2.2 g. of 6-hydroxy-2-naphthyl-α-methylacetic acid, 50 ml. of acetic anhydride, and 100 mg. of p-toluenesulfonic acid is stirred for four hours at 50° C. The mixture is evaporated, water is added, and the mixture is extracted with diethyl ether which is washed with water to neutrality, dried over sodium sulfate, and evaporated to yield 6-acetoxy-2-naphthyl-α-methylacetic acid.

Workup

  1. additionA mixture of 2.2 g
  2. customThe mixture is evaporated
  3. additionwater is added
  4. extractionthe mixture is extracted with diethyl ether which
  5. washis washed with water to neutrality
  6. dry with materialdried over sodium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-607ee582e244404e86011673e47df1c8
Source dataset
uspto-grants-1976_12
Patent number
US03998966

Reaction notes

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