Benzoic Acid → 4-Acetoxy-3-acetylbenzoic acid

HRID 26718Notes

Reaction equation

HRID 26718 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[C:11](=[O:13])[CH3:12].C(Cl)Cl.[C:17](OC(=O)C)(=[O:19])[CH3:18].C(O)(=O)C1C=CC=CC=1>C(N(CC)CC)C.O1CCCC1>[C:17]([O:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[C:11](=[O:13])[CH3:12])(=[O:19])[CH3:18]

Participants

7

Reactant 4

HCID 243Benzoic AcidHCID 6344DichloromethaneHCID 7918Acetic AnhydrideHCID 91792453-Acetyl-4-hydroxybenzoic acid

Product 1

HCID 213223944-Acetoxy-3-acetylbenzoic acid

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

To a suspension of 2.3 g. of 4-hydroxy-3-acetylbenzoic acid in 100 ml. of methylene chloride and 100 ml. of tetrahydrofuran, a mixture of 1.5 g. of triethylamine, 1.6 g. of 4-N-dimethylaminopyridine and 1.5 g. of acetic anhydride is added. The reaction mixture is heated at 50° for one hour. The solution is extracted with ethyl acetate, the organic layer washed with water and dilute hydrochloric acid and evaporated to dryness to yield 2.1 g. of the benzoic acid product. NMR in CDCl3

Workup

  1. additionTo a suspension of 2.3 g
  2. temperatureThe reaction mixture is heated at 50° for one hour
  3. extractionThe solution is extracted with ethyl acetate
  4. washthe organic layer washed with water and dilute hydrochloric acid
  5. customevaporated to dryness
  6. customto yield 2.1 g

Sources & evidence

ORD record
ord-8565aed6498241c8809f1e76110e1797
Source dataset
uspto-grants-1979_04
Patent number
US04151297

Reaction notes

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