Hydrochloric Acid → HCID 53730416, compound

HRID 1938645Notes

Reaction equation

HRID 1938645 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([C:24]2[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH2:32][CH2:33][CH2:34][Cl:35])=[CH:26][CH:25]=2)(O)[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>CO>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([C:24]2[CH:25]=[CH:26][C:27]([O:30][CH2:31][CH2:32][CH2:33][CH2:34][Cl:35])=[CH:28][CH:29]=2)=[CH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 54059133HCID 54059133, compound

Product 1

HCID 53730416HCID 53730416, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Combine 1-(4-benzyloxyphenyl)-1-(4-(4-chlorobutyloxy) phenyl)-2-phenyl ethanol (1.0 g, 21.0 mmol) and methanol (2 mL). Add aqueous 2M hydrochloric acid solution (4 mL). Heat to reflux. After 2 hours, concentrate at 65° C. to remove most of the methanol. Cool to ambient temperature and extract with dichloromethane. Dry the organic layer over MgSO4, filter, and dry in vacuo to give 1-(4-benzyloxyphenyl)-1-(4-(4-chlorobutyloxy) phenyl)-2-phenyl ethylene: Rf =0.50 (silica gel, 30% ethyl acetate/hexane).

Workup

  1. temperatureHeat to reflux
  2. concentrationconcentrate at 65° C.
  3. customto remove most of the methanol
  4. extractionextract with dichloromethane
  5. dry with materialDry the organic layer over MgSO4
  6. filtrationfilter
  7. customdry in vacuo

Sources & evidence

ORD record
ord-a8016ca7254f4bcd99106015bcae917b
Source dataset
uspto-grants-1997_12
Patent number
US05693674

Reaction notes

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