Sodium Hydroxide → 2-[(4-Fluorophenyl)thio]benzenemethanol

HRID 2049684Notes

Reaction equation

HRID 2049684 reaction equation
[Na].[H-].COCCO[Al+]OCCOC.[F:14][C:15]1[CH:20]=[CH:19][C:18]([S:21][C:22]2[CH:30]=[CH:29][CH:28]=[CH:27][C:23]=2[C:24](O)=[O:25])=[CH:17][CH:16]=1.[OH-].[Na+]>C1C=CC=CC=1>[F:14][C:15]1[CH:20]=[CH:19][C:18]([S:21][C:22]2[CH:30]=[CH:29][CH:28]=[CH:27][C:23]=2[CH2:24][OH:25])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 144187682-[(4-Fluorophenyl)sulfanyl]benzoic acidHCID 86736934HCID 86736934, compound

Product 1

HCID 541878152-[(4-Fluorophenyl)thio]benzenemethanol

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

36.1 ml of 70% sodium-bis-(2-methoxyethoxy)aluminum hydride in benzene are added dropwise over a one hour span to a stirring mixture of 15 g of 2-(4-fluorophenylthio)benzoic acid in 150 ml of benzene under nitrogen at ambient temperature. After total addition, the reaction mixture is stirred for an additional 30 minutes and then permitted to stand for 4 days. Thereafter, the reaction mixture is cooled to 0° C. before 100 mls of 10% sodium hydroxide are added with stirring. Following this addition, the layers separate and the aqueous layer is extracted twice with 100 ml portions of benzene. The combined benzene solutions are successively washed twice with 100 ml portions of water, washed once with a 60 ml portion of a saturated sodium chloride solution and dried, providing 2-(4-fluorophenylthio)benzyl alcohol.

Workup

  1. additionAfter total addition
  2. waitto stand for 4 days
  3. additionare added
  4. stirringwith stirring
  5. additionthis addition
  6. customthe layers separate
  7. extractionthe aqueous layer is extracted twice with 100 ml portions of benzene
  8. washThe combined benzene solutions are successively washed twice with 100 ml portions of water
  9. washwashed once with a 60 ml portion of a saturated sodium chloride solution
  10. customdried

Sources & evidence

ORD record
ord-91c7c4e4f65841c5bc24bd382341c1d6
Source dataset
uspto-grants-1980_04
Patent number
US04198420

Reaction notes

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