Hydrochloric Acid → 1-Chloro-5,5-dimethylnonan-4-one

HRID 26598Notes

Reaction equation

HRID 26598 reaction equation
[CH3:1][C:2]([Mg]Cl)([CH3:7])[CH2:3][CH2:4][CH2:5][CH3:6].[Mg].ClC(C)(C)CCCC.[Cl:19][CH2:20][CH2:21][CH2:22][C:23](Cl)=[O:24].Cl>CCOCC>[Cl:19][CH2:20][CH2:21][CH2:22][C:23](=[O:24])[C:2]([CH3:7])([CH3:1])[CH2:3][CH2:4][CH2:5][CH3:6]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 783704-Chlorobutyryl chlorideHCID 1382242-Chloro-2-methylhexaneHCID 5462224MagnesiumHCID 178443943HCID 178443943, compound

Product 1

HCID 203860731-Chloro-5,5-dimethylnonan-4-one

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Four hundred ml. of a solution in ether of 1,1-dimethylpentylmagnesium chloride prepared from magnesium (24.3 g., 1.0 mole) and 1-chloro-1,1-dimethylpentane (134.5 g., 1.0 mole) according to the procedure of Whitmore and Badertscher [J. Am. Chem. Soc., 55, 1559 (1933)] is added dropwise with stirring to 4-chlorobutyryl chloride (197 g., 1.4 moles) in ether (400 ml.) during 6 hours. The reaction mixture is stirred for an additional 12 hours. It is then poured into a mixture of ice and dilute hydrochloric acid. The ether layer is separated, washed with water, and dried over sodium sulfate. The ether is evaporated and the residue distilled at aspirator vacuum through a Vigreaux column to yield the product as a colorless oil.

Workup

  1. additionis added dropwise
  2. customThe ether layer is separated
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. customThe ether is evaporated
  6. distillationthe residue distilled at aspirator vacuum through a Vigreaux column

Sources & evidence

ORD record
ord-6bef68f4d0124a8aa5a5f891c79f1214
Source dataset
uspto-grants-1979_04
Patent number
US04150235

Reaction notes

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