Hydrochloric Acid → HCID 86751679, compound

HRID 1938635Notes

Reaction equation

HRID 1938635 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1([C:13]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)(O)[CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH2:8]1.Cl>CO>[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1([C:13]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[CH:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:8]=[CH:9][CH:10]=[CH:11][CH2:12]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67686974HCID 67686974, compound

Product 1

HCID 86751679HCID 86751679, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Combine 1-(4-chlorobutoxy)phenyl-1,2-diphenyl ethanol (17.0 kg, 20.2 mol) and methanol (30 L). Add aqueous 3M hydrochloric acid solution (40 L). Heat to reflux. After 2 hours, remove most of the methanol by distillation and cool the aqueous reaction mixture. Extract with chloroform. Extract the organic layer with aqueous saturated sodium carbonate solution. Separate the organic layer and evaporate in vacuo to give (E and Z)-1-(4-chlorobutoxy)phenyl-1,2-diphenyl ethylene.

Workup

  1. temperatureHeat to reflux
  2. customremove most of the methanol by distillation
  3. temperaturecool the aqueous reaction mixture
  4. extractionExtract with chloroform
  5. extractionExtract the organic layer with aqueous saturated sodium carbonate solution
  6. customSeparate the organic layer
  7. customevaporate in vacuo

Sources & evidence

ORD record
ord-a4e22f3b19ff4205a85423f53f756530
Source dataset
uspto-grants-1997_12
Patent number
US05693674

Reaction notes

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