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

HRID 1376994Notes

Reaction equation

HRID 1376994 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:10][C:11]1[C:12]([C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:13][C:14]2[O:18][CH:17]=[CH:16][C:15]=2[C:19]=1[C:20]([CH3:23])([CH3:22])[CH3:21])(=O)C.O.Cl>O1CCCC1>[C:20]([C:19]1[C:15]2[CH:16]=[CH:17][O:18][C:14]=2[CH:13]=[C:12]([C:24]([CH3:27])([CH3:26])[CH3:25])[C:11]=1[OH:10])([CH3:23])([CH3:22])[CH3:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 118223325-Acetoxy-4,6-di-tert-butylbenzofuranHCID 21226445Aluminium lithium hydride

Product 1

HCID 117707334,6-Di-tert-butyl-5-hydroxybenzofuranYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium aluminum hydride (1.31 g) was suspended in tetrahydrofuran (150 ml) under a nitrogen atmosphere. A solution of 5-acetoxy-4,6-di-tert-butylbenzofuran (10 g) in tetrahydrofuran (100 ml) was added dropwise to the suspension under cooling with ice. After heating under reflux for 3 h, the mixture was cooled to room temperature and, after addition of water and 10% aqueous HCl (100 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 [8.3 g (yield, 98%)].

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-d18182c9e8a34efaa82592cbb913f42e
Source dataset
uspto-grants-1997_09
Patent number
US05663373

Reaction notes

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