Benzophenone → Benzenemethanol, .alpha.-methyl-.alpha.-phenyl-

HRID 865623Notes

Reaction equation

HRID 865623 reaction equation
[C:1]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[NH4+].[CH2:17]1COCC1>>[C:2]1([C:1]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)([OH:8])[CH3:17])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 3102BenzophenoneHCID 8028TetrahydrofuranHCID 25517Ammonium Chloride

Product 1

HCID 69031Benzenemethanol, .alpha.-methyl-.alpha.-phenyl-

Procedure

To this reaction mixture was added dropwise a liquid mixture of 182.22 g (1.1 mol) of benzophenone (3a; R1,R2 =H) and 364 ml of dry THF at 35° to 40° C. over a period of 30 minutes. This mixture was stirred first at that temperature for 2 hours and then at that temperature for 13 hours to complete the reaction. The resulting solution was added to 1,400 g of cooled 10% aqueous ammonium chloride solution with cooling with ice. The mixture was stirred for 30 minutes, allowed to stand, and then subjected to liquid separation, followed by washing with aqueous common salt solution, drying with magnesium sulfate, and concentration to obtain 200.23 g of crude 1,1-diphenylethanol (theoretical yield based on the benzophenone, 98.6%).

Workup

  1. additionTo this reaction mixture was added dropwise
  2. waitat that temperature for 13 hours to complete
  3. customthe reaction
  4. temperaturewith cooling with ice
  5. stirringThe mixture was stirred for 30 minutes
  6. customsubjected to liquid separation
  7. washby washing with aqueous common salt solution
  8. dry with materialdrying with magnesium sulfate, and concentration

Sources & evidence

ORD record
ord-2c95e21813cd456194bf2f6af76e5951
Source dataset
uspto-grants-1996_10
Patent number
US05567560

Reaction notes

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