Hydrochloric Acid → E-3-(3-phenoxyphenyl)-1-chloroprop-2-ene

HRID 2165982Notes

Reaction equation

HRID 2165982 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:14](O)[CH:15]=[CH2:16])[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:18].O>C(OCC)C>[O:1]([C:8]1[CH:9]=[C:10](/[CH:14]=[CH:15]/[CH2:16][Cl:18])[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 129613931-(3-Phenoxyphenyl)prop-2-en-1-ol

Product 1

HCID 19915310E-3-(3-phenoxyphenyl)-1-chloroprop-2-ene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1-(3-Phenoxyphenyl)prop-2-en-1-ol (0.05 g) was dissolved in diethyl ether (2 cm3) which had been previously saturated with hydrogen chloride gas, and the solution was stirred at the ambient temperature for 2 hours. Water was added to the mixture and the products extracted into further diethyl ether. The combined ethereal layers were dried over anhydrous magnesium sulphate and the solvent evaporated under reduced pressure. The residual oil was purified by column chromatography on a silica gel support, eluted with hexane containing 5% by volume ethyl acetate, to give E-3-(3-phenoxyphenyl)-1-chloroprop-2-ene (0.03 g).

Workup

  1. extractionthe products extracted into further diethyl ether
  2. dry with materialThe combined ethereal layers were dried over anhydrous magnesium sulphate
  3. customthe solvent evaporated under reduced pressure
  4. customThe residual oil was purified by column chromatography on a silica gel support
  5. washeluted with hexane containing 5% by volume ethyl acetate

Sources & evidence

ORD record
ord-da8a4d9f1bd3466888da9a1eb04a0075
Source dataset
uspto-grants-1990_07
Patent number
US04942264

Reaction notes

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