Water → 2-Phenoxybenzyl alcohol

HRID 1274219Notes

Reaction equation

HRID 1274219 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.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[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

5

Reactant 3

HCID 962WaterHCID 752372-Phenoxybenzoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 36601112-Phenoxybenzyl alcoholYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled (0°), stirred, solution of o-phenoxybenzoic acid (2.14 g, 10.0 mmol) in dry tetrahydrofuran (20 ml) under argon was added lithium aluminium hydride (0.19 g, 5 mmol) added in portions over 10 minutes. After a further 1 hour, water was added cautiously until effervescence ceased. The reaction mixture was partitioned between ethyl acetate and water and filtered. The organic layer was washed with saturated sodium hydrogen carbonate solution followed by water and dried over MgSO4. Evaporation of solvent gave crude product (1.59 g, 80%). δH (CDCl3) 2.01 (1H, br t), 4.77 (2H, d, J 4.9 Hz), 6.9-7.5 (9H, m) ppm

Workup

  1. temperatureTo a cooled (0°)
  2. additionadded in portions over 10 minutes
  3. customThe reaction mixture was partitioned between ethyl acetate and water
  4. filtrationfiltered
  5. washThe organic layer was washed with saturated sodium hydrogen carbonate solution
  6. dry with materialdried over MgSO4
  7. customEvaporation of solvent

Sources & evidence

ORD record
ord-7c9ee5958122442f9445e6862272d0b3
Source dataset
uspto-grants-2000_12
Patent number
US06156774

Reaction notes

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