Water → 4-(4-Methylphenyl)butanol

HRID 1751855Notes

Reaction equation

HRID 1751855 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][C:17](O)=[O:18])=[CH:10][CH:9]=1.O.[OH-].[Na+]>CCOCC>[CH3:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][CH2:17][OH:18])=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 782794-p-Tolylbutyric acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 1040094-(4-Methylphenyl)butanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To lithium aluminum hydride (427 mg, 11.2 mmol) suspended in dry ether (5 ml) at 0° C. is added 1 g of 4-(4-methylphenyl) butanoic acid (5.614 mmol) dissolved in dry ether (10 ml) over a period of 30 minutes. The reaction mixture is then warmed to room temperature and stirred for 4 hours. Water (0.43 ml), NaOH (15% solution, 0.43 g) and water (1.29 ml) are then added successively and the resulting solution is stirred for 30 minutes. The precipitate is filtered and washed with ether and dried. This is then concentrated and purified by flash chromatography (silica gel; ethyl acetate/hexanes) as the eluting medium.

Workup

  1. stirringthe resulting solution is stirred for 30 minutes
  2. filtrationThe precipitate is filtered
  3. washwashed with ether
  4. customdried
  5. concentrationThis is then concentrated
  6. custompurified by flash chromatography (silica gel; ethyl acetate/hexanes) as the eluting medium

Sources & evidence

ORD record
ord-4d2b611cd46c4a6394af44e7c24ce3bf
Source dataset
uspto-grants-2015_10
Patent number
US09161997B2

Reaction notes

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