Reaction #54874

Reaction equation

5-chloro-2-pentanone

1-bromopentane

magnesium

Acetic anhydride

→

title compound

1-Chloro-4-acetoxy-4-methylnonane

Solvents

Water

ether

Conditions

Workup

1. 1
   Temperaturecooled to 15° C
2. 2
   workup.WAITto stand for 20 hours
3. 3
   Otherthe ether layer is separated
4. 4
   Washwashed with brine
5. 5
   Dryingdried over sodium sulfate
6. 6
   workup.DISTILLATIONDistillation

Procedure

To the Grignard reagent prepared from 1-bromopentane (4.8 g., 0.04 mole) and magnesium (0.96 g., 0.04 mole) in ether is added 5-chloro-2-pentanone (6.0 g., 0.04 mole). The reaction mixture is stirred at 25° C. for 1 hour and then cooled to 15° C. Acetic anhydride (6 ml., excess) is added carefully and the solution is allowed to stand for 20 hours. Water is added, and the ether layer is separated, washed with brine, and dried over sodium sulfate. Distillation affords the title compound in 4.3 g. (46%) yield, b.p. 88° C. (0.1 mm.).

Source