Acetic Acid → 4-Benzoyl-5-hydroxybenzocyclobutene-1-carboxylic acid

HRID 1248361Notes

Reaction equation

HRID 1248361 reaction equation
[C:1]([C:9]1[C:18]([OH:19])=[CH:17][C:12]2[C:13]([CH2:15][OH:16])=[CH:14][C:11]=2[CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=[O:22])C>[O-2].[O-2].[O-2].[Cr+6]>[C:1]([C:9]1[C:18]([OH:19])=[CH:17][C:12]2[C:13]([C:15]([OH:22])=[O:16])=[CH:14][C:11]=2[CH:10]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 202794314-Benzoyl-5-hydroxybenzocyclobutene-1-methanol

Product 1

HCID 202794244-Benzoyl-5-hydroxybenzocyclobutene-1-carboxylic acid

Reagents, catalysts & solvents 1

HCID 10219390chromium (VI) trioxideCatalyst

Procedure

1.0 g of 4-benzoyl-5-hydroxybenzocyclobutene-1-methanol is dissolved in 50 ml of acetic acid and then 4.0 g of chromium trioxide are added in portions. The whole is stirred for 16 hours at 40°, concentrated to dryness by evaporation under reduced pressure, taken up in 20 ml of water and extracted by shaking with 80 ml of dichloromethane. The organic phase is dried over magnesium sulphate and concentrated by evaporation. After recrystallisation of the residue from ether/hexane, 4-benzoyl-5-hydroxybenzocyclobutene-1-carboxylic acid is obtained having a melting point of 167°-169°.

Workup

  1. concentrationconcentrated to dryness by evaporation under reduced pressure
  2. extractionextracted
  3. stirringby shaking with 80 ml of dichloromethane
  4. dry with materialThe organic phase is dried over magnesium sulphate
  5. concentrationconcentrated by evaporation
  6. customAfter recrystallisation of the residue from ether/hexane

Sources & evidence

ORD record
ord-66c03d01d7504eeebda7c78269fa7ba2
Source dataset
uspto-grants-1985_06
Patent number
US04523030

Reaction notes

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