Hydrochloric Acid → 4-Chloro-2-[(4-chlorophenyl)ethen-2-yl]phenol

HRID 421011Notes

Reaction equation

HRID 421011 reaction equation
[Cl:1][C:2]1[CH:9]=[C:6]([CH:7]=O)[C:5]([OH:10])=[CH:4][CH:3]=1.[Cl-].[Cl:12][C:13]1[CH:38]=[CH:37][C:16](C[P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:15][CH:14]=1.[C:39](=O)([O-])[O-].[K+].[K+].Cl>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([C:7]([C:16]2[CH:37]=[CH:38][C:13]([Cl:12])=[CH:14][CH:15]=2)=[CH2:39])[CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 124815-Chloro-salicylaldehydeHCID 2733546(4-Chlorobenzyl)triphenylphosphonium chloride

Product 1

HCID 666573014-Chloro-2-[(4-chlorophenyl)ethen-2-yl]phenolYield 8.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5-Chlorosalicylaldehyde (313 mg, 2 mmol) and 4-chlorobenzyltriphenyl-phosphonium chloride (847 mg, 2 mmol) were dissolved in N,N-dimethylfomamide (20 mL). Potassium carbonate (1.382 g, 10 mmol) dissolved in water (10 mL) was added, and the mixture was refluxed for 5 hours. After cooling, the reaction mixture was poured into 2 N hydrochloric acid and extracted with ethyl acetate. After the organic layer was washed with water and brine, dried over anhydrous magnesium sulfate, the residue obtained by evaporation under reduced pressure was purified by chromatography on silica gel (n-hexane:ethyl acetate=3:1) to give the title compound (44.6 mg, 8.4%) as a light gray solid.

Workup

  1. additionwas added
  2. temperaturethe mixture was refluxed for 5 hours
  3. temperatureAfter cooling
  4. extractionextracted with ethyl acetate
  5. washAfter the organic layer was washed with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe residue obtained by evaporation under reduced pressure
  8. customwas purified by chromatography on silica gel (n-hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-87093531cff042a39b00c4a8ca57ecf8
Source dataset
uspto-grants-2012_01
Patent number
US08097759B2

Reaction notes

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