Acetic Acid → 3-(2-Hydroxy-4-methylbenzoyl)benzoic acid

HRID 1720167Notes

Reaction equation

HRID 1720167 reaction equation
C(O[C:8]1[CH:24]=[CH:23][C:11]([C:12]([C:14]2[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=2)[C:17]([OH:19])=[O:18])=[O:13])=[C:10](C)[CH:9]=1)CCCCC.[C:26](O)(=O)C.S(=O)(=O)(O)O.[OH2:35]>>[OH:35][C:10]1[CH:9]=[C:8]([CH3:26])[CH:24]=[CH:23][C:11]=1[C:12]([C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=1)[C:17]([OH:19])=[O:18])=[O:13]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 1118Sulfuric AcidHCID 224203873-(4-n-Hexyloxy-2-methylbenzoyl)benzoic acid

Product 1

HCID 224203823-(2-Hydroxy-4-methylbenzoyl)benzoic acid

Procedure

A mixture of 3-(2-hydroxy-4-methylbenzoyl)benzonitrile (5.78 g; see Example 29), acetic acid (48 g), and a solution of 75% sulfuric acid (48 g) is refluxed for 3 hours. The resulting mixture is diluted with water (100 ml) and extracted with ether (3×75 ml) followed by methylene chloride (2×75 ml). The combined extracts are dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue is chromatographed on silica gel (methylene chloride then hexanes:ether:acetic acid; 50:50:1). The resulting yellow solid is recrystallized from ligroin/isopropyl ether to yield 3-(2-hydroxy-4-methylbenzoyl)benzoic acid (3.62 g), m.p. 198°-215° C.

Workup

  1. extractionextracted with ether (3×75 ml)
  2. dry with materialThe combined extracts are dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue is chromatographed on silica gel (methylene chloride
  6. customThe resulting yellow solid is recrystallized from ligroin/isopropyl ether

Sources & evidence

ORD record
ord-628e1e0d6e154d1aa9aa6d53c6d0c69d
Source dataset
uspto-grants-1996_04
Patent number
US05504244

Reaction notes

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