Acetic Anhydride → 1-Chloro-4-acetoxy-4-methylnonane

HRID 26596

Reaction equation

HRID 26596 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[Mg].[Cl:8][CH2:9][CH2:10][CH2:11]C(=O)C.[C:15]([O:18][C:19](=O)[CH3:20])(=[O:17])[CH3:16]>CCOCC.O>[Cl:8][CH2:9][CH2:10][CH2:11][C:19]([O:18][C:15](=[O:17])[CH3:16])([CH3:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 80571-BromopentaneHCID 799932-Pentanone, 5-chloro-HCID 5462224Magnesium

Product 1

HCID 203860911-Chloro-4-acetoxy-4-methylnonane

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
25 °C

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.).

Workup

  1. temperaturecooled to 15° C
  2. waitto stand for 20 hours
  3. customthe ether layer is separated
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. distillationDistillation

Sources & evidence

ORD record
ord-128778f48ccd4e9884777d39704485c0
Source dataset
uspto-grants-1979_04
Patent number
US04150235

Linked notes

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