Reaktion #304925

Reaktionsgleichung

trimethyl borate

hydrochloric acid

n-butyllithium

sodium hydroxide

hydrogen peroxide

1-Bromo-3-tert-butyl-5-(1,1-dimethoxyethyl)-2-methoxybenzene

→

title compound

1-(3-tert-Butyl-5-hydroxy-4-methoxyphenyl)ethanone

Lösungsmittel

EA

water

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITto come to RT within 2 h
2. 2
   workup.STIRRINGAfter stirring at RT for 2 h
3. 3
   workup.WAITthe mixture was left
4. 4
   workup.WAITto stand overnight
5. 5
   SonstigeAfter removing the EA phase
6. 6
   Trocknenthis was dried over magnesium sulfate
7. 7
   Einengenconcentrated
8. 8
   SonstigeThe residue was purified
9. 9
   Sonstigesilica gel (330 g cartridge, n-heptane/EA gradient of 0-50% within 60 min)

Vorschrift

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.

Quelle