Water → 4-(4-Methylphenyl)butanol

HRID 1751875Notes

Reaction equation

HRID 1751875 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 allowed to warm to room temperature and stirred for 4 hours. Water (0.43 ml), NaOH (15% solution, 0.43 g) and water (1.29 ml) were then added successively and the resulting solution is stirred for 30 minutes. The resulting precipitate is filtered and washed with ether and dried. The filtrate is then concentrated and purified by flash chromatography using ethyl acetate-hexanes as the eluting medium.

Workup

  1. stirringthe resulting solution is stirred for 30 minutes
  2. filtrationThe resulting precipitate is filtered
  3. washwashed with ether
  4. customdried
  5. concentrationThe filtrate is then concentrated
  6. custompurified by flash chromatography

Sources & evidence

ORD record
ord-48eeff840c3f4c02af47112e42925b0a
Source dataset
uspto-grants-2015_10
Patent number
US09161997B2

Reaction notes

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