Water → HCID 54552991, compound

HRID 1389176Notes

Reaction equation

HRID 1389176 reaction equation
Br[CH2:2][C:3](=[O:24])[CH:4]=[P:5]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[Cl:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[OH:32].[OH-].[K+].O>C(O)C>[Cl:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[O:32][CH2:2][C:3](=[O:24])[CH:4]=[P:5]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 72452-ChlorophenolHCID 14797Potassium HydroxideHCID 12546501HCID 12546501, compound

Product 1

HCID 54552991HCID 54552991, compoundYield 50.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Bromo-2-oxopropylidenetriphenylphosphorane (8.0 g) was added to a solution of o-chlorophenol (3.8 g) and potassium hydroxide (1.56 g) in anhydrous ethanol (60 ml), and the resulting mixture was heated at reflux for 2 hours and was then poured into water (200 ml). The mixture was extracted with methylene chloride and the extract was washed with dilute aqueous sodium hydroxide solution (2 N) and with water, dried over magnesium sulphate, and evaporated. The residual solid was recrystallised from a mixture of petroleum ether (b.p. 60°-80° C.) and ethyl acetate, to give 3-(2-chlorophenoxy)-2-oxopropylidenetriphenylphosphorane (4.5 g), m.p. 102°-104° C. A further recrystallisation from a similar solvent gave a purer sample, m.p. 107°-109° C. [elemental analysis: C, 73.1; H, 5.3; P, 7.0%. C27H22ClO2P requires C, 72.9; H, 5.0; P, 6.95%. νmax 715, 750, 1110, 1405, 1440, 1485 and 1550 cm-1 ].

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 2 hours
  3. extractionThe mixture was extracted with methylene chloride
  4. washthe extract was washed with dilute aqueous sodium hydroxide solution (2 N) and with water
  5. dry with materialdried over magnesium sulphate
  6. customevaporated
  7. customThe residual solid was recrystallised from a mixture of petroleum ether (b.p. 60°-80° C.) and ethyl acetate

Sources & evidence

ORD record
ord-5210b221a2624fc99c0cb14deb82845f
Source dataset
uspto-grants-1981_01
Patent number
US04243683

Reaction notes

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