Reaction #42760

Reaction equation

water

1-[2-Hydroxy-4-(4-methoxy-benzyloxy)-phenyl]-ethanone

Triethylamine

Isobutyryl chloride

→

Isobutyric acid 2-acetyl-5-(4-methoxy-benzyloxy)-phenyl ester

Solvents

dichloromethane

Conditions

Workup

1. 1
   Temperaturewhile warming to room temperature
2. 2
   Otherthe dichloromethane layer is separated
3. 3
   Washwashed with saturated brine (100 ml)
4. 4
   Dryingdried (MgSO4)
5. 5
   workup.ADDITIONtreated with activated charcoal (300 mg)
6. 6
   Filtrationfiltered
7. 7
   Otherevaporated
8. 8
   Otherto give a pale pink solid

Procedure

1-[2-Hydroxy-4-(4-methoxy-benzyloxy)-phenyl]-ethanone (9.11 g, 0.034 mol) is dissolved in dry dichloromethane (120 ml) under an atmosphere of dry argon. Triethylamine (5.14 ml, 0.037 mol) and 4-dimethylaminopyridine (0.204 g, 1.67 mmol) are added, and the mixture is cooled to 0° C. using an ice-water bath. Isobutyryl chloride (3.89 ml, 0.037 mol) is then added dropwise, and the mixture is stirred while warming to room temperature. The mixture is poured into water (100 ml), and the dichloromethane layer is separated, washed with saturated brine (100 ml), dried (MgSO4), treated with activated charcoal (300 mg), filtered and evaporated to give a pale pink solid.

Source