Hydrochloric Acid → (4-Phenoxyphenyl)methanol

HRID 1610309Notes

Reaction equation

HRID 1610309 reaction equation
[C:1]1([O:7][C:8]2[CH:16]=[CH:15][C:11]([C:12](O)=[O:13])=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.B.Cl>O1CCCC1>[C:1]1([O:7][C:8]2[CH:16]=[CH:15][C:11]([CH2:12][OH:13])=[CH:10][CH:9]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 751824-Phenoxybenzoic acid

Product 1

HCID 826195(4-Phenoxyphenyl)methanolYield 87.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-(phenyloxy)benzoic acid (10.4 g, 48.7 mmol) in tetrahydrofuran (30 ml) was added 1M tetrahydrofuran solution of borane (63 ml, 63 mmol) at room temperature and the mixture was stirred overnight. 1N Hydrochloric acid was added to the reaction solution for quenching and the mixture was extracted with ethyl acetate (100 ml×2). The extract was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate) and recrystallized from hexane to give (4-(phenyloxy)phenyl)methanol (8.51 g, 87%).

Workup

  1. customfor quenching
  2. extractionthe mixture was extracted with ethyl acetate (100 ml×2)
  3. washThe extract was washed successively with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate)
  7. customrecrystallized from hexane

Sources & evidence

ORD record
ord-b37126780a154a45baa8b67d6ce0b81f
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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