Hydrochloric Acid → 2-Phenoxybenzyl alcohol

HRID 736029Notes

Reaction equation

HRID 736029 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-].Cl.O>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

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 752372-Phenoxybenzoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 36601112-Phenoxybenzyl alcohol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add 2-Phenoxy-benzoic acid (1 g, 4.67 mmol), in several portions, to a suspension of Lithium aluminium hydride (372 mg, 9.33 mmol) in dry THF (20 ml) at room temperature and stir. After 1 h, add aqueous 1M HCl dropwise carefully, then pour into H2O and extract three times with Et2O. Combine the organic phases, dry over Na2SO4 and concentrate at vacuum to yield pure (2-Phenoxy-phenyl)-methanol as courless oil. Add aqueous concentrated HBr (16 ml) to a solution of (2-Phenoxy-phenyl)-methanol (900 mg, 4.5 mmol) in CH2Cl2 (5 ml) and stir at room temperature. After 1 h. separate the organic phase and wash the aqueous one with CH2Cl2. Combine organic phases, wash with H2, dry over Na2SO4 and concentrate at vacuum to obtain a residue. Purify the residue by column chromatography on silica gel eluting with hexane:CH2Cl2, 2:1 to afford 1-Bromomethyl-2-phenoxy-benzene as colourless oil. 1H-NMR (CDCl3, 200 MHz): δ 7.44-7.01 (m, 8H), 6.84 (d, J=1.2 and 8.0 Hz, 1H), 4.60 (s, 2H).

Workup

  1. extractionextract three times with Et2O
  2. dry with materialdry over Na2SO4
  3. concentrationconcentrate at vacuum

Sources & evidence

ORD record
ord-8085a772e60944eba870980063868d14
Source dataset
uspto-grants-2009_09
Patent number
US07595315B2

Reaction notes

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