Diethyl Ether → HCID 13076860, compound

HRID 1278290Notes

Reaction equation

HRID 1278290 reaction equation
CCOCC.[CH:6]1([Mg]Br)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([OH:29])=[C:19]([CH:28]=1)[C:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:21]>C1C=CC=CC=1>[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([OH:29])=[C:19]([C:20]([CH:6]2[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[OH:21])[CH:28]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 6799Chlorohydroxy benzophenoneHCID 178419651HCID 178419651, compound

Product 1

HCID 13076860HCID 13076860, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

295 ml of an ether solution titrating 1.23 M/liter of cyclohexyl magnesium bromide were added over 2 hours at 40°-45° C. to a solution of 5-chloro-2-hydroxy-benzophenone in 150 ml of anhydrous benzene and the ether was distilled while being replaced with benzene. The mixture was refluxed for 4 hours, was cooled and poured into a liter of ice and ammonium chloride. The mixture was extracted 3 times with 400 ml of ether and the combined ether phases were washed with water, dried over magnesium sulfate and evaporated to dryness under reduced pressure. The residue was taken up in 250 ml of cyclohexane to obtain 15.9 g of 5-chloro-2-hydroxy-α-cyclohexyl-α-phenyl-benzene-methanol melting at 170° C.

Workup

  1. distillationthe ether was distilled
  2. temperatureThe mixture was refluxed for 4 hours
  3. temperaturewas cooled
  4. additionpoured into a liter of ice and ammonium chloride
  5. extractionThe mixture was extracted 3 times with 400 ml of ether
  6. washthe combined ether phases were washed with water
  7. dry with materialdried over magnesium sulfate
  8. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-ade6d798ffa54928b3b682a2bb988166
Source dataset
uspto-grants-1981_07
Patent number
US04281012

Reaction notes

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