Sodium Hydroxide → HCID 178524044, compound

HRID 1248343Notes

Reaction equation

HRID 1248343 reaction equation
C[O:2][C:3]([C:5]1[C:8]2[CH:9]=[C:10]([OH:22])[C:11]([C:13](=[O:21])[C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=3)=[CH:12][C:7]=2[CH:6]=1)=[O:4].[OH-].[Na+]>CCOCC>[Cl:20][C:16]1[CH:15]=[C:14]([CH:19]=[CH:18][CH:17]=1)[C:13]([C:11]1[C:10]([OH:22])=[CH:9][C:8]2[C:5]([C:3]([OH:4])=[O:2])=[CH:6][C:7]=2[CH:12]=1)=[O:21]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178496932HCID 178496932, compound

Product 1

HCID 178524044HCID 178524044, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

12.1 g of 4-(m-chlorobenzoyl)-5-hydroxybenzocyclobutene- 1-carboxylic acid methyl ester are dissolved in 120 ml of ether; 100 ml of 2N aqueous sodium hydroxide solution are added and the whole is stirred well for 15 minutes at room temperature. The ether phase is separated off and washed with water. The strongly yellow-coloured aqueous phase is washed with ether. The combined aqueous phases are rendered acidic with concentrated hydrochloric acid and extracted thoroughly with methylene chloride. The combined methylene chloride extracts are dried over magnesium sulphate and concentrated by evaporation. Crystallisation of the residue from ether/petroleum ether yields 4-(m-chlorobenzoyl)-5-hydroxybenzocyclobutene-1-carboxylic acid in the form of yellow crystals having a melting point of 138°-139°.

Workup

  1. customThe ether phase is separated off
  2. washwashed with water
  3. washThe strongly yellow-coloured aqueous phase is washed with ether
  4. extractionextracted thoroughly with methylene chloride
  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-fd245eb9531e484b96f4ed2b530753ce
Source dataset
uspto-grants-1985_06
Patent number
US04523030

Reaction notes

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