Water → (4-Propylphenyl)methanol

HRID 914478Notes

Reaction equation

HRID 914478 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([C:10]1[CH:18]=[CH:17][C:13]([C:14](O)=[O:15])=[CH:12][CH:11]=1)[CH2:8][CH3:9].O.[OH-].[Na+]>C(OCC)C>[CH2:7]([C:10]1[CH:18]=[CH:17][C:13]([CH2:14][OH:15])=[CH:12][CH:11]=1)[CH2:8][CH3:9]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 1376014-Propylbenzoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 2760472(4-Propylphenyl)methanolYield 107.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Lithium aluminum hydride (1.16 g) was suspended in diethyl ether (100 mL), a solution (50 mL) of 4-propylbenzoic acid (5.0 g) in diethyl ether was added under ice-cooling, and the mixture was heated under reflux for 2.5 hr. The reaction mixture was ice-cooled, and water (3.0 mL) and aqueous sodium hydroxide solution (1 mol/L, 12 mL) were successively added dropwise. After warming to room temperature, the mixture was stirred for 30 min. The reaction mixture was directly filtered through celite, and the filtrate was evaporated under reduced pressure to give the title compound (4.9 g) as a colorless oil.

Workup

  1. temperaturecooling
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 2.5 hr
  4. temperaturecooled
  5. filtrationThe reaction mixture was directly filtered through celite
  6. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-1736463b6a1747318e228e35ff4c31a1
Source dataset
uspto-grants-2011_09
Patent number
US08026370B2

Reaction notes

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