Hydrochloric Acid → HCID 15485720, compound

HRID 2305436Notes

Reaction equation

HRID 2305436 reaction equation
C([O:4][C:5]1[C:6]([C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:7][C:8]2[O:12][C:11]([CH2:14][OH:15])([CH3:13])[CH2:10][C:9]=2[C:16]=1[C:17]([CH3:20])([CH3:19])[CH3:18])(=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C.Cl>O1CCCC1>[C:17]([C:16]1[C:9]2[CH2:10][C:11]([CH2:14][OH:15])([CH3:13])[O:12][C:8]=2[CH:7]=[C:6]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:5]=1[OH:4])([CH3:20])([CH3:18])[CH3:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 154857195-Acetoxy-4,6-di-t-butyl-2-hydroxymethyl-2-methyl-2,3-dihydrobenzofuranHCID 21226445Aluminium lithium hydride

Product 1

HCID 15485720HCID 15485720, compoundYield 73.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 500 mg of 5-acetoxy-4,6-di-t-butyl-2-hydroxymethyl-2-methyl-2,3-dihydrobenzofuran in 7 ml of tetrahydrofuran was added dropwise to a suspension of 114 mg of lithium aluminum hydride in 3 ml of tetrahydrofuran under nitrogen atmosphere. The reaction mixture was heated under reflux for 2 hours. After allowing the mixture to attain room temperature, ethyl acetate was added dropwise, 10% hydrochloric acid was added thereto, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (20% ethyl acetate in n-hexane) to yield 320 mg (73%) of 4,6-di-t-butyl-5-hydroxy-2-hydroxymethyl-2-methyl-2,3-dihydrobenzofuran as a white solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 2 hours
  3. customto attain room temperature
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography (20% ethyl acetate in n-hexane)

Sources & evidence

ORD record
ord-ef59b276eaf148f0a875c0b772eb4ebd
Source dataset
uspto-grants-2002_08
Patent number
US06440999B1

Reaction notes

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