Water → (3-Isopropoxyphenyl)methanol

HRID 1610643Notes

Reaction equation

HRID 1610643 reaction equation
[CH:1]([O:4][C:5]1[CH:6]=[C:7]([CH:13]=[CH:14][CH:15]=1)[C:8](OCC)=[O:9])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[CH:1]([O:4][C:5]1[CH:6]=[C:7]([CH:13]=[CH:14][CH:15]=1)[CH2:8][OH:9])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 22261418Ethyl 3-isopropoxybenzoate

Product 1

HCID 2759474(3-Isopropoxyphenyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 3-isopropyloxybenzoate (12.0. g, 61.8 mmol) in tetrahydrofuran (100 ml) was added lithium aluminum hydride (3.52 g, 92.7 mmol) by small portions under ice-cooling. The mixture was stirred at room temperature for 1 hr. and water (10 ml) was added under ice-cooling to allow decomposition. Insoluble material was filtered off and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (hexane:ethyl acetate=3:1) to give the objective substance (10.0 g, 97%) as an oil.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. filtrationInsoluble material was filtered off
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (hexane:ethyl acetate=3:1)
  6. customto give the objective substance (10.0 g, 97%) as an oil

Sources & evidence

ORD record
ord-4a5251236d074b49a520daef3613eac7
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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