Hydrochloric Acid → 1-(3-Tert-butyl-5-hydroxy-4-methoxyphenyl)ethanone

HRID 217743Notes

Reaction equation

HRID 217743 reaction equation
Br[C:2]1[CH:7]=[C:6]([C:8](OC)([O:10]C)[CH3:9])[CH:5]=[C:4]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:3]=1[O:18][CH3:19].C([Li])CCC.B(OC)(OC)[O:26]C.[OH-].[Na+].OO.Cl>C1COCC1.CC(=O)OCC.O>[C:14]([C:4]1[CH:5]=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=[C:2]([OH:26])[C:3]=1[O:18][CH3:19])([CH3:17])([CH3:16])[CH3:15]

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 8470Trimethyl borateHCID 14798Sodium HydroxideHCID 230937191-Bromo-3-tert-butyl-5-(1,1-dimethoxyethyl)-2-methoxybenzeneHCID 178418339Butyllithium

Product 1

HCID 581369461-(3-Tert-butyl-5-hydroxy-4-methoxyphenyl)ethanone

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-Bromo-3-tert-butyl-5-(1,1-dimethoxyethyl)-2-methoxybenzene (O4.070; 36.3 g) was dissolved in THF (1 l), n-butyllithium (52.6 ml; 2.5 M in hexane) was added dropwise at −75° C. under argon, and the mixture was stirred for a further 30 min. Then trimethyl borate (37.3 ml) was added dropwise and the mixture was allowed to come to RT within 2 h. Subsequently, sodium hydroxide (4.4 g, dissolved in 10 ml of water) and hydrogen peroxide solution (62.3 ml; 35% in water) were added successively. After stirring at RT for 2 h, the mixture was left to stand overnight. Then water and EA were added and the mixture was acidified with hydrochloric acid. After removing the EA phase, this was dried over magnesium sulfate and concentrated. The residue was purified using silica gel (330 g cartridge, n-heptane/EA gradient of 0-50% within 60 min). 14 g of the title compound were obtained.

Workup

  1. waitto come to RT within 2 h
  2. stirringAfter stirring at RT for 2 h
  3. waitthe mixture was left
  4. waitto stand overnight
  5. customAfter removing the EA phase
  6. dry with materialthis was dried over magnesium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified
  9. customsilica gel (330 g cartridge, n-heptane/EA gradient of 0-50% within 60 min)

Sources & evidence

ORD record
ord-1b8d0497b8e4424d9fc54a8048307590
Source dataset
uspto-grants-2012_06
Patent number
US08198272B2

Reaction notes

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