Methyl 4-(benzyloxy)-2-hydroxybenzoate → 5-Benzyloxy-2-hydroxymethylphenol

HRID 643946Notes

Reaction equation

HRID 643946 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C[O:8][C:9](=O)[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:12][C:11]=1[OH:24]>C1COCC1>[CH2:17]([O:16][C:13]1[CH:14]=[CH:15][C:10]([CH2:9][OH:8])=[C:11]([OH:24])[CH:12]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 225489Methyl 4-(benzyloxy)-2-hydroxybenzoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 251384215-Benzyloxy-2-hydroxymethylphenol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a 1.0M solution of LiAlH4 (22 mL) in THF at 0° C. is added dropwise a solution of 4-(benzyloxy)-2-hydroxybenzoic acid methyl ester (2.84 g, 11 mmol) in THF (15 mL). The mixture is stirred for 2 h, then quenched by the careful addition of 1 mL of saturated Na2SO4 solution. The mixture is warmed to ambient temperature and extracted with Et2O. The organic layer is washed with water, sat. NaCl and dried over sodium sulfate. The solvent is removed under reduced pressure to afford 5-benzyloxy-2-hydroxymethylphenol as a white solid: 1H NMR (DMSO-d6) δ 9.28 (s, 1H), 7.42-7.31 (m, 5H), 7.11 (d, J=8.34 Hz, 1H), 6.44-6.40 (m, 2H), 5.01 (s, 2H), 4.75-4.72 (m, 1H), 4.38 (d, J=5.56 Hz, 2H); (M−H)−=229.

Workup

  1. customquenched by the careful addition of 1 mL of saturated Na2SO4 solution
  2. extractionextracted with Et2O
  3. washThe organic layer is washed with water, sat. NaCl
  4. dry with materialdried over sodium sulfate
  5. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-26a93a797fbe4bd2b61068cb883c63c4
Source dataset
uspto-grants-2010_04
Patent number
US07700633B2

Reaction notes

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