2-Phenoxybenzoic acid → 2-Phenoxybenzyl alcohol

HRID 1078037Notes

Reaction equation

HRID 1078037 reaction equation
[O:1]([C:8]1[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10](O)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B.C1COCC1>C1COCC1>[O:1]([C:8]1[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=1[CH2:10][OH:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 752372-Phenoxybenzoic acidHCID 2723981Borane;tetrahydrofuran

Product 1

HCID 36601112-Phenoxybenzyl alcohol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of o-phenoxybenzoic acid (19.0 g, 88.7 mmol) in THF (100 mL) at 0° C. under N2 was added BH3.THF (133 mL, 1.0M in THF) over a period of 1 h, keeping the temperature below 5° C. The reaction mixture was then stirred at room temperature for 2 h. It was quenched with H2O, then 1N aqueous HCl. The two layers were separated. The aqueous layer was extracted with EtOAc. The combined organic mixture was washed with brine, dried over MgSO, and concentrated to a light yellow oil (16.9 g). The crude product was used in the next step without further purification. MS m/e 183.1, [M+H-H2O]+ ; 1H NMR (300 MHz, CDCl3): δ 2.08 (t, 1H, OH), 4.76 (d, 2H, CH2Ar), 6.82-7.48 (m, 9H, ArH). ##STR64##

Workup

  1. customthe temperature below 5° C
  2. customIt was quenched with H2O
  3. customThe two layers were separated
  4. extractionThe aqueous layer was extracted with EtOAc
  5. washThe combined organic mixture was washed with brine
  6. dry with materialdried over MgSO
  7. concentrationconcentrated to a light yellow oil (16.9 g)
  8. customThe crude product was used in the next step without further purification

Sources & evidence

ORD record
ord-cb49d72e749a415c80fe7f1c4c5d2879
Source dataset
uspto-grants-1996_08
Patent number
US05545651

Reaction notes

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