Water → HCID 10976648, compound

HRID 1722494Notes

Reaction equation

HRID 1722494 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]([C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][CH2:19][C:20](O)=[O:21])=[CH:13][CH:12]=1)([CH3:10])[CH3:9].O.[OH-].[Na+]>C1COCC1.C(OCC)C>[CH3:10][C:8]([C:11]1[CH:12]=[CH:13][C:14]([CH2:17][CH2:18][CH2:19][CH2:20][OH:21])=[CH:15][CH:16]=1)([CH3:7])[CH3:9]

Participants

7

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 50189424-(4-tert-butylphenyl)butanoic AcidHCID 21226445Aluminium lithium hydride

Product 1

HCID 10976648HCID 10976648, compoundYield 97.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred suspension of lithium aluminum hydride (4.0 g, 0.105 mol) in THF (100 mL) at 0° C. under a nitrogen atmosphere was added a solution of 4-[4-(1,1-dimethylethyl)-phenyl]butanoic acid (10.31 g, 0.0455 mol) in THF (80 mL). The reaction was heated to reflux for 6 hours. The reaction was cooled to 0° C. and water (4 mL), 15% NaOH (4 mL) and water (12 mL) were carefully added. Ethyl ether (150 mL) was added, the mixture warmed to ambient temperature, and the precipitated salts were removed by filtration. Removal of solvent gave 9.15 g of 4-[4-(1,1-dimethylethyl)phenyl]-butanol as a colorless oil.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 6 hours
  3. temperaturethe mixture warmed to ambient temperature
  4. customthe precipitated salts were removed by filtration
  5. customRemoval of solvent

Sources & evidence

ORD record
ord-3f98c29e59424beb82e54ee0bc67da41
Source dataset
uspto-grants-1989_08
Patent number
US04855462

Reaction notes

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