Ammonium Chloride → HCID 18433150, compound

HRID 1452368Notes

Reaction equation

HRID 1452368 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:10][C:11]1[C:16]([C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:15][C:14]([O:21][CH2:22][CH2:23][CH3:24])=[C:13]([CH3:25])[C:12]=1[C:26]([CH3:29])([CH3:28])[CH3:27])(=O)C.[Cl-].[NH4+]>O1CCCC1>[C:26]([C:12]1[C:13]([CH3:25])=[C:14]([O:21][CH2:22][CH2:23][CH3:24])[CH:15]=[C:16]([C:17]([CH3:20])([CH3:19])[CH3:18])[C:11]=1[OH:10])([CH3:28])([CH3:29])[CH3:27]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 18433157HCID 18433157, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18433150HCID 18433150, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium aluminum hydride (100 mg) was suspended in tetrahydrofuran (5 ml) under a nitrogen atmosphere. A solution of the 1-acetoxy-2,6-di-tert-butyl-3-methyl-4-propyloxybenzen in tetrahydrofuran (5 ml) was added to the suspension and the mixture was refluxed for 3 h. A saturated aqueous solution of ammonium chloride was added to the reaction mixture under ice cooling and the precipitate was filtered off together with the anhydrous sodium sulfate. The filtrate was concentrated and purified by silica gel chromatography (10% ethyl acetate in n-hexane) to afford 2,6-di-tert-butyl-3-methyl-4-propyloxyphenol (150 mg) as a colorless oil.

Workup

  1. temperaturethe mixture was refluxed for 3 h
  2. filtrationthe precipitate was filtered off together with the anhydrous sodium sulfate
  3. concentrationThe filtrate was concentrated
  4. custompurified by silica gel chromatography (10% ethyl acetate in n-hexane)

Sources & evidence

ORD record
ord-56ae7c35debb46878af96bb595aa914a
Source dataset
uspto-grants-1997_02
Patent number
US05606089

Reaction notes

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