Methanol → beta-Phenylphenethyl alcohol

HRID 1496696

Reaction equation

HRID 1496696 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[C:11]1([CH:17]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:18](OC)=[O:19])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.CO.[OH-].[Na+]>C1(C)C=CC=CC=1.ClCCl>[C:22]1([CH:17]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:18][OH:19])[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 77019Methyl alpha-phenylbenzeneacetateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 74662beta-Phenylphenethyl alcoholYield 92.4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent3×

Procedure

To a 500 mL three-opening flask was slowly added a solution of diisobutylaluminum hydride in toluene (282 mL, 1 mol/L) at −30° C. After stirring, to the resulting mixture was slowly added a solution of methyl 2,2-diphenylacetate (21 g, 92.8 mmol) 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, to the resulting mixture was slowly added methanol (10 mL), dichloromethane (100 mL) and an aqueous sodium hydroxide solution (100 mL, 1 mol/L) at −20° C. After the completion of reaction, to the reaction solution was added dichloromethane for extraction. The organic phase was washed with water, dried over anhydrous sodium sulfate, and evaporated to remove the solvent to produce 2,2-diphenyl ethanol (17 g) in a yield of 92.4%.

Workup

  1. additionAfter the completion of dropwise addition
  2. customAfter the completion of reaction
  3. customat −20° C
  4. customAfter the completion of reaction
  5. extractionfor extraction
  6. washThe organic phase was washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. customevaporated
  9. customto remove the solvent

Sources & evidence

ORD record
ord-c5b4b4af12be43909fb27b62397ea093
Source dataset
uspto-grants-2015_12
Patent number
US09198902B2

Linked notes

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