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

HRID 1900521Notes

Reaction equation

HRID 1900521 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-9988ad543a0a48ba9667619d1bf909fe
Source dataset
uspto-grants-1996_11
Patent number
US05574178

Reaction notes

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