Sodium sulfate decahydrate → [4-(Diphenylmethoxy)-3-isobutylphenyl]methanol

HRID 507994Notes

Reaction equation

HRID 507994 reaction equation
[C:1]1([CH:7]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[O:8][C:9]2[CH:18]=[CH:17][C:12]([C:13](OC)=[O:14])=[CH:11][C:10]=2[CH2:19][CH:20]([CH3:22])[CH3:21])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[C:1]1([CH:7]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[O:8][C:9]2[CH:18]=[CH:17][C:12]([CH2:13][OH:14])=[CH:11][C:10]=2[CH2:19][CH:20]([CH3:22])[CH3:21])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 23157404Methyl 4-(diphenylmethoxy)-3-isobutylbenzoate

Product 1

HCID 23157345[4-(Diphenylmethoxy)-3-isobutylphenyl]methanolYield 101%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-(diphenylmethoxy)-3-isobutylbenzoate (0.45 g, 1.20 mmol) in tetrahydrofuran (20 mL) was added lithium aluminum hydride (60 mg, 1.58 mmol) by small portions under ice-cooling. The mixture was stirred under ice-cooling for 2 hr, sodium sulfate decahydrate (1.2 g, 2.30 mmol) was added to the reaction solution by small portions, and the mixture was stirred at room temperature for 1 hr. The insoluble material was filtered off, and the filtrate was concentrated to give the title compound (420 mg, yield 100%) as a colorless oil.

Workup

  1. temperaturecooling
  2. temperaturecooling for 2 hr
  3. stirringthe mixture was stirred at room temperature for 1 hr
  4. filtrationThe insoluble material was filtered off
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-f94b99147b0442d09b3231b7d7c71642
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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