Hydrochloric Acid → 4,6-Di-tert-butyl-5-hydroxybenzofuran

HRID 1452383Notes

Reaction equation

HRID 1452383 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:10][C:11]1[C:12]([C:32]([CH3:35])([CH3:34])[CH3:33])=[CH:13][C:14]2[O:18][C:17](CCCCCCCC)=[CH:16][C:15]=2[C:27]=1[C:28]([CH3:31])([CH3:30])[CH3:29])(=O)C.O.Cl>O1CCCC1>[C:28]([C:27]1[C:15]2[CH:16]=[CH:17][O:18][C:14]=2[CH:13]=[C:12]([C:32]([CH3:35])([CH3:34])[CH3:33])[C:11]=1[OH:10])([CH3:31])([CH3:30])[CH3:29]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 184331765-Acetoxy-4,6-di-tert-butyl-2-octylbenzofuranHCID 21226445Aluminium lithium hydride

Product 1

HCID 117707334,6-Di-tert-butyl-5-hydroxybenzofuranYield 132.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium aluminum hydride (0.26 g) was suspended in tetrahydrofuran (50 ml) under a nitrogen atmosphere and a solution of 5-acetoxy-4,6-di-tert-butyl-2-octylbenzofuran (2.7 g) in tetrahydrofuran (20 ml) was added to the suspension under cooling with ice. After heating under reflux for 3 h, the mixture was cooled to room temperature and water was added dropwise. After adding 10% aqueous HCl (50 ml), the mixture was subjected to extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated. The concentrate was purified by silica gel chromatography (10% ethyl acetate in n-hexane) to afford 4,6-di-tert-butyl-5-hydroxybenzofuran [2.2 g (yield, 92%)] as a colorless oil.

Workup

  1. temperatureunder cooling with ice
  2. temperatureAfter heating
  3. temperatureunder reflux for 3 h
  4. extractionthe mixture was subjected to extraction with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe concentrate was purified by silica gel chromatography (10% ethyl acetate in n-hexane)

Sources & evidence

ORD record
ord-8a53ec1b69114ef09110d4c75989e120
Source dataset
uspto-grants-1997_02
Patent number
US05606089

Reaction notes

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