Hydrochloric Acid → HCID 22918662, compound

HRID 1452364Notes

Reaction equation

HRID 1452364 reaction equation
[C:1]([C:5]1[C:6](=[O:17])[C:7]([C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:8][C:9](=[O:12])[C:10]=1[CH3:11])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].[CH3:20][OH:21].Cl>C(Cl)Cl>[C:1]([C:5]1[C:10]([CH3:11])=[C:9]([O:12][CH:20]2[CH2:10][CH2:5][CH2:1][CH2:2][O:21]2)[CH:8]=[C:7]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:6]=1[OH:17])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 4311764Sodium borohydrideHCID 21707797HCID 21707797, compound

Product 1

HCID 22918662HCID 22918662, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,6-di-tert-butyl-3-methyl-1,4-benzoquinone (49 g) was dissolved in methylene chloride (300 ml) and sodium borohydride (15 g) was added to the solution under a nitrogen atmosphere. After adding methanol (30 ml) dropwise, the mixture was stirred for 3 h, poured into 5% HCl under ice cooling, and subjected to extraction with methylene chloride. The extract was washed with water, dried over anhydrous sodium sulfate and the solvent was distilled off. The residue was dissolved in methylene chloride (200 ml) and, after adding 3,4-2H-dihydropyran (26 ml) and a catalytic amount of paratoluenesulfonic acid, the mixture was stirred overnight at room temperature. The reaction mixture was washed with water, dried over anhydrous sodium sulfate and the solvent was distilled off. The residue was purified by silica gel chromatography (10% ethyl acetate in n-hexane) to afford 2,6-di-tert-butyl-3-methyl-4-tetrahydropyranyloxyphenol [54.4 g (yield, 81%)] as a colorless oil.

Workup

  1. extractionsubjected to extraction with methylene chloride
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off
  5. dissolutionThe residue was dissolved in methylene chloride (200 ml)
  6. additionafter adding 3,4-2H-dihydropyran (26 ml)
  7. stirringa catalytic amount of paratoluenesulfonic acid, the mixture was stirred overnight at room temperature
  8. washThe reaction mixture was washed with water
  9. dry with materialdried over anhydrous sodium sulfate
  10. distillationthe solvent was distilled off
  11. customThe residue was purified by silica gel chromatography (10% ethyl acetate in n-hexane)

Sources & evidence

ORD record
ord-2ea9322fff6046fe98f8b7c79dc26e58
Source dataset
uspto-grants-1997_02
Patent number
US05606089

Reaction notes

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