4-Hydroxybenzoic Acid → Benzoic acid, 4-(acetyloxy)-

HRID 1447615Notes

Reaction equation

HRID 1447615 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[O:11]1CC[CH2:13][CH2:12]1.C(Cl)Cl.C(OC(=O)C)(=O)C>CN(C)C1C=CN=CC=1.C(N(CC)CC)C>[C:12]([O:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1)(=[O:11])[CH3:13]

Participants

7

Reactant 4

HCID 1354-Hydroxybenzoic AcidHCID 6344DichloromethaneHCID 7918Acetic AnhydrideHCID 8028Tetrahydrofuran

Product 1

HCID 16865Benzoic acid, 4-(acetyloxy)-

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8471TriethylamineSolvent

Procedure

To 20 g. of 4-hydroxybenzoic acid in suspension in 150 ml. of tetrahydrofuran (THF) and 150 ml. methylene chloride, 35 g. of triethylamine, 35 g. of acetic anhydride and 3 g. of 4-dimethylaminopyridine are added and the mixture refluxed for 30 minutes. The solvents are thereafter evaporated under reduced pressure and 6N hydrochloric acid is added to the residue. The resulting slurry is filtered, washed with water and dried, affording 20 g. of the captioned compound.

Workup

  1. temperaturethe mixture refluxed for 30 minutes
  2. customThe solvents are thereafter evaporated under reduced pressure and 6N hydrochloric acid
  3. additionis added to the residue
  4. filtrationThe resulting slurry is filtered
  5. washwashed with water
  6. customdried
  7. customaffording 20 g

Sources & evidence

ORD record
ord-30f43bf67d1b4a1ca275e7e88228dc39
Source dataset
uspto-grants-1979_12
Patent number
US04177280

Reaction notes

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