Methanol → 3,3-Diphenylpropanol

HRID 1496691Notes

Reaction equation

HRID 1496691 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[C:11]1([CH:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:18][C:19](OCC)=[O:20])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.CO.O>C1(C)C=CC=CC=1.ClCCl>[C:24]1([CH:17]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:18][CH2:19][OH:20])[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 962WaterHCID 344791Ethyl 3,3-diphenylpropanoateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 299083,3-DiphenylpropanolYield 100.2%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

To a 30 L reaction kettle was slowly added a solution of diisobutylaluminum hydride in toluene (15 L, 1 mol/L) at −20° C. After stirring, to the resulting mixture was slowly added a solution of ethyl 3,3-diphenyl-1-propanate (1200 g, 4.7 mol) in dichloromethane dropwisely. After the completion of dropwise addition, the reaction was conducted at 25° C. for 12 hours. After the completion of reaction monitored by TLC, the reaction solution was divided into three parts. 200 mL methanol and 1000 mL water were slowly added respectively at −20° C. to quench off the reaction. The reaction solutions were combined and extracted with dichloromethane. The organic phase was dried over anhydrous sodium sulfate, and evaporated to remove the solvent to produce an oily crude product of 3,3-diphenyl-1-propanol (1000 g), which was directly used in the next reaction.

Workup

  1. customTo a 30 L reaction kettle
  2. additionAfter the completion of dropwise addition
  3. customAfter the completion of reaction
  4. customto quench off
  5. customthe reaction
  6. extractionextracted with dichloromethane
  7. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  8. customevaporated
  9. customto remove the solvent

Sources & evidence

ORD record
ord-f7ed78a286ee419088cbf627c2240521
Source dataset
uspto-grants-2015_12
Patent number
US09198902B2

Reaction notes

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