Hydrochloric Acid → HCID 22918662, compound

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. Mass 320(M+)

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)

ORD record

ord-d8b1594603b94d96ac0be1e14686579c

Source dataset

uspto-grants-1996_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05574178