Oxalyl chloride → HCID 67189596, compound

HRID 1665928Notes

Reaction equation

HRID 1665928 reaction equation
[C:1]([CH:4]1[CH2:9][C:8]([CH3:11])([CH3:10])[CH2:7][CH2:6][C:5]1=[O:12])(=O)[CH3:2].C(Cl)(=O)C([Cl:16])=O>C(Cl)(Cl)Cl>[Cl:16][C:1](=[C:4]1[CH2:9][C:8]([CH3:11])([CH3:10])[CH2:7][CH2:6][C:5]1=[O:12])[CH3:2]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 11389626HCID 11389626, compound

Product 1

HCID 67189596HCID 67189596, compoundYield 57.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

At 0° C., a solution of 2-acetyl-4,4-dimethyl-cyclohexanone (5.00 g, 29.7 mmol) in chloroform (15 mL) is treated with oxalyl chloride (7.54 g, 59.4 mmol). The mixture is heated to 60° C. and stirred for 15 min before it is poured onto water. The organic phase is separated, washed with sat. aq. NaHCO3 solution and brine, dried over MgSO4 and evaporated to dryness to give crude 2-(1-chloro-ethylidene)-4,4-dimethyl-cyclohexanone (3.2 g, containing regio-isomer) as a brown oil, LC-MS: tR=1.00 min.

Workup

  1. additionis poured onto water
  2. customThe organic phase is separated
  3. washwashed with sat. aq. NaHCO3 solution and brine
  4. dry with materialdried over MgSO4
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-4b3007dc98f84138b065c58d06cdb653
Source dataset
uspto-grants-2011_10
Patent number
US08039644B2

Reaction notes

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