Water → HCID 20777166, compound

HRID 2242350Notes

Reaction equation

HRID 2242350 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9](=O)[C:10]1[CH:15]=[C:14]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH:13]=[CH:12][C:11]=1[O:20][CH3:21].O>C(OCC)C>[C:16]([C:14]1[CH:13]=[CH:12][C:11]([O:20][CH3:21])=[C:10]([CH2:9][OH:8])[CH:15]=1)([CH3:19])([CH3:17])[CH3:18]

Participants

5

Reactant 3

HCID 962WaterHCID 15724682Methyl 5-(tert-butyl)-2-methoxybenzoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 20777166HCID 20777166, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
20 °C

Procedure

A solution of 1.0M lithium aluminium hydride in diethyl ether (27.0 ml, 27.0 mmol) was added dropwise over 10 min to a solution of 5-tert-butyl-2-methoxybenzoic acid methyl ester (5.00 g, 22.4 mmol) in diethyl ether (90 ml) under nitrogen, maintaining temperature between 0° C. and 5° C. When addition was complete, the reaction was stirred at 20° C. for 3.5 h, then again cooled to 0° C. Addition of water (5 ml) destroyed any excess reagent and filtration of the resulting mixture through dicalite removed the unwanted inorganic residue. After drying the resulting filtrate with magnesium sulfate, evaporation under reduced pressure afforded (5-tert-butyl-2-methoxyphenyl)methanol as a pale yellow gum (4.20 g, 21.6 mmol, 96%).

Workup

  1. temperaturemaintaining temperature between 0° C. and 5° C
  2. additionWhen addition
  3. temperatureagain cooled to 0° C
  4. customdestroyed
  5. filtrationany excess reagent and filtration of the resulting mixture through dicalite
  6. customremoved the unwanted inorganic residue
  7. customAfter drying the resulting filtrate
  8. customwith magnesium sulfate, evaporation under reduced pressure

Sources & evidence

ORD record
ord-4451b1e2a15241d99a1e2c6e93c52063
Source dataset
uspto-grants-2010_03
Patent number
US07671080B2

Reaction notes

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