Acetic Acid → 2-(Acetyloxy)-5-ethyl-4-methylbenzoic acid

HRID 596900Notes

Reaction equation

HRID 596900 reaction equation
[CH2:1]([C:3]1[CH:11]=[C:7]([C:8]([OH:10])=[O:9])[C:6]([OH:12])=[CH:5][C:4]=1[CH3:13])[CH3:2].[C:14](OC(=O)C)(=[O:16])[CH3:15].C(O)(=O)C>O>[C:14]([O:12][C:6]1[CH:5]=[C:4]([CH3:13])[C:3]([CH2:1][CH3:2])=[CH:11][C:7]=1[C:8]([OH:10])=[O:9])(=[O:16])[CH3:15]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 7918Acetic AnhydrideHCID 123664205-Ethyl-2-hydroxy-4-methylbenzoic acid

Product 1

HCID 123664232-(Acetyloxy)-5-ethyl-4-methylbenzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5-ethyl-4-methylsalicylic acid (15.00 g), acetic anhydride (80 ml) and acetic acid (80 ml) was heated under reflux for 1.5 hours, poured into water (1 l) and allowed to stand overnight. The solid formed was filtered off and recrystallised from benzene to give 2-acetoxy-5-ethyl-4-methylbenzoic acid, m.p. 132°-134° C. (Found; C, 64.71; H, 6.46; C12H14O4 requires; C, 64.85; H, 6.35).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1.5 hours
  3. customThe solid formed
  4. filtrationwas filtered off
  5. customrecrystallised from benzene

Sources & evidence

ORD record
ord-a94376496f5d44808559706704a3a0f6
Source dataset
uspto-grants-1977_03
Patent number
US04012407

Reaction notes

Loading…