Oxalyl chloride → HCID 86645768, compound

HRID 1676111Notes

Reaction equation

HRID 1676111 reaction equation
C(Cl)(=O)C([Cl:4])=O.O[CH:8]=[C:9]([CH2:15][CH:16]([CH3:18])[CH3:17])[C:10](=[O:14])[CH:11]([CH3:13])[CH3:12]>C(Cl)(Cl)Cl>[Cl:4][CH:8]=[C:9]([CH2:15][CH:16]([CH3:18])[CH3:17])[C:10](=[O:14])[CH:11]([CH3:13])[CH3:12]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 86645767HCID 86645767, compound

Product 1

HCID 86645768HCID 86645768, compoundYield 174.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
-10 °C

Procedure

Over a period of 20 min, a solution of oxalylchloride (6.5 mL, 9.6 g, 75.6 mmol) in chloroform (10 mL) is added slowly to a solution of 1-hydroxy-2-isobutyl-4-methyl-pent-1-en-3-one (7.35 g, 43.2 mmol) in chloroform (100 mL) cooled to −10° C. The mixture is stirred for further 30 min, quenched with ice (100 g) and 1 N aq. NaOH (100 mL). When the quite violent gas evolution ceases the phases are separated. The organic phase is washed with 1 N aq. NaOH (3×75 mL) and 1 N aq. NaH2PO4 (75 mL), dried (MgSO4), filtered and evaporated to give crude 1-chloro-2-isobutyl-4-methyl-pent-1-en-3-one (14.2 g) as a brown oil.

Workup

  1. customquenched with ice (100 g) and 1 N aq. NaOH (100 mL)
  2. customare separated
  3. washThe organic phase is washed with 1 N aq. NaOH (3×75 mL) and 1 N aq. NaH2PO4 (75 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-ff9c8c33802840beaae2fc2642ce14e6
Source dataset
uspto-grants-2011_08
Patent number
US08003800B2

Reaction notes

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