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

HRID 437848Notes

Reaction equation

HRID 437848 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-c1a9255f0251434b9273c92b88f565b6
Source dataset
uspto-grants-1977_06
Patent number
US04032544

Reaction notes

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