Water → 4-Benzoyl-5-hydroxybenzocyclobutene-1-carboxylic acid

HRID 1248341Notes

Reaction equation

HRID 1248341 reaction equation
C[O:2][C:3]([C:5]1[C:8]2[CH:9]=[C:10]([OH:21])[C:11]([C:13](=[O:20])[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:12][C:7]=2[CH:6]=1)=[O:4].[OH-].[Na+].O>CCOCC>[C:13]([C:11]1[C:10]([OH:21])=[CH:9][C:8]2[C:5]([C:3]([OH:4])=[O:2])=[CH:6][C:7]=2[CH:12]=1)(=[O:20])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 54244647HCID 54244647, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

14 g of 4-benzoyl-5-hydroxybenzocyclobutene-1-carboxylic acid methyl ester are dissolved in 150 ml of ether and the solution is added to 62 ml of 2N aqueous sodium hydroxide solution and 25 ml of water. This mixture is vigorously stirred for 1 hour at room temperature. The ether phase is separated off and extracted once with 75 ml of water. The aqueous phase is washed once with 75 ml of ether. The combined aqueous phases are rendered acidic with 2N aqueous hydrochloric acid and extracted 3 times with 100 ml of methylene chloride each time. The combined methylene chloride extracts are dried over magnesium sulphate and concentrated by evaporation. Crystallisation of the residue from ether/petroleum ether yields 4-benzoyl-5-hydroxybenzocyclobutene-1-carboxylic acid in the form of yellow crystals having a melting point of 167°-169°.

Workup

  1. customThe ether phase is separated off
  2. extractionextracted once with 75 ml of water
  3. washThe aqueous phase is washed once with 75 ml of ether
  4. extractionextracted 3 times with 100 ml of methylene chloride each time
  5. dry with materialThe combined methylene chloride extracts are dried over magnesium sulphate
  6. concentrationconcentrated by evaporation
  7. customCrystallisation of the residue from ether/petroleum ether

Sources & evidence

ORD record
ord-92ca51e1ba084e1bbcd6c4a7431875f6
Source dataset
uspto-grants-1985_06
Patent number
US04523030

Reaction notes

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