Acetone → [2-(4-Fluorobenzyl)phenyl]methanol

HRID 2378495Notes

Reaction equation

HRID 2378495 reaction equation
[F:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][C:7]2[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=2[C:9](O)=[O:10])=[CH:4][CH:3]=1.CC(C)=O.[OH-].[Na+]>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C:7]2[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=2[CH2:9][OH:10])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 14798Sodium HydroxideHCID 117363592-(4-Fluorobenzyl)benzoic acid

Product 1

HCID 23001227[2-(4-Fluorobenzyl)phenyl]methanol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
2.5 °C

Procedure

In an inertized flask containing 2-(4-fluoro-benzyl)-benzoic acid (1 eq.), toluene (0.8 L/mol) is added and the vessel is cooled down to 0-5° C. Sodium dihydro-bis(2-methoxyethoxy)aluminate (“RedAl”) (1 M in toluene, 2.3 eq.) is added dropwise and the reaction mixture is stirred at 5° C. during 16 hours. Acetone (3 eq.) is added dropwise at 5° C. and the mixture is stirred during 15 minutes. The temperature is allowed to rise to 25° C. A sodium hydroxide solution (5 eq.) is added and the mixture is stirred vigorously during 20 minutes. The organic layer is separated and washed again with a slightly acidic aqueous solution. The organic layer is filtered over Dicalite and used further in the next step.

Workup

  1. additionis added
  2. stirringthe mixture is stirred during 15 minutes
  3. customto rise to 25° C
  4. stirringthe mixture is stirred vigorously during 20 minutes
  5. customThe organic layer is separated
  6. washwashed again with a slightly acidic aqueous solution
  7. filtrationThe organic layer is filtered over Dicalite

Sources & evidence

ORD record
ord-e3c6c407d78a4d049ce29d8a54e17971
Source dataset
uspto-grants-2008_12
Patent number
US07470809B2

Reaction notes

Loading…