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

HRID 973335Notes

Reaction equation

HRID 973335 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 brine 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 and brine
  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-81f2ed12d2ff4899a12f74c1d2efa295
Source dataset
uspto-grants-1977_10
Patent number
US04055597

Reaction notes

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