Sulfuric Acid → (4-Phenoxyphenyl)methanol

HRID 2080038Notes

Reaction equation

HRID 2080038 reaction equation
[BH4-].[Na+].S(=O)(=O)(O)O.[O:8]([C:15]1[CH:23]=[CH:22][C:18]([C:19](O)=[O:20])=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[OH-].[Na+]>C(OCC)C.O1CCCC1.C(OCC)(=O)C.CO>[O:8]([C:15]1[CH:16]=[CH:17][C:18]([CH2:19][OH:20])=[CH:22][CH:23]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

9

Reactant 4

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 751824-Phenoxybenzoic acidHCID 4311764Sodium borohydride

Product 1

HCID 826195(4-Phenoxyphenyl)methanol

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of sodium borohydride (2.20 g, 58.3 mmol) and concentrated sulfuric acid in diethyl ether (1.6 mL) was added to a solution of 4-phenoxybenzoic acid (5.0 g, 23.3 mmol) in tetrahydrofuran (20 mL) that had been cooled on an ice bath, and the solution was stirred for 4 hours at room temperature. The reaction solution was cooled on an ice bath, methanol was added, then, the solution was allowed to room temperature and stirred for 30 minutes. This reaction solution was cooled again, ethyl acetate and an aqueous solution of 2N sodium hydroxide were added for partitioning, the organic layer was washed with 10% sodium chloride water, dried over anhydrous magnesium sulfate, and the solvent was evaporated to obtain 4-phenoxybenzyl alcohol (4.669, quantitatively) as a colorless solid. This 4-phenoxybenzyl alcohol was used to carry out an analogous reaction to Preparation Example 2, and the title compound (886 mg) was obtained as a pale brown solid.

Workup

  1. temperaturehad been cooled on an ice bath
  2. temperatureThe reaction solution was cooled on an ice bath
  3. customwas allowed to room temperature
  4. stirringstirred for 30 minutes
  5. temperatureThis reaction solution was cooled again
  6. customfor partitioning
  7. washthe organic layer was washed with 10% sodium chloride water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customthe solvent was evaporated

Sources & evidence

ORD record
ord-f966aa41f052492883650d2d3bb7a6b4
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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