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

HRID 1576476Notes

Reaction equation

HRID 1576476 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-27ee9e02a6f94e1b8638044b0b648da4
Source dataset
uspto-grants-1976_09
Patent number
US03980699

Reaction notes

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