Acetyl chloride → 1-Acetoxy-5-naphthoic acid

HRID 614573Notes

Reaction equation

HRID 614573 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]([OH:14])=[O:13].[C:15](Cl)(=[O:17])[CH3:16]>C1C=CC=CC=1>[C:15]([O:1][C:2]1[C:3]2[CH:4]=[CH:5][CH:6]=[C:7]([C:12]([OH:14])=[O:13])[C:8]=2[CH:9]=[CH:10][CH:11]=1)(=[O:17])[CH3:16]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 755315-Hydroxy-1-naphthoic acid

Product 1

HCID 4582121-Acetoxy-5-naphthoic acid

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 20 g. of 5-hydroxy-1-naphthoic acid in 200 ml. of benzene and 40 ml. of acetyl chloride is refluxed for 3 hours. Solvent and excess acetyl chloride are evaporated. The mixture is dissolved in methanol (150 ml.) and water (20 ml.) added. After 15 minutes, addition of more water results in the precipitation of 1-acetoxy-5-naphthoic acid.

Workup

  1. customSolvent and excess acetyl chloride are evaporated
  2. dissolutionThe mixture is dissolved in methanol (150 ml.)
  3. additionwater (20 ml.) added
  4. additionaddition of more water

Sources & evidence

ORD record
ord-1baa52067a1d454dbb10069acdf8461e
Source dataset
uspto-grants-1979_03
Patent number
US04145443

Reaction notes

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