Sodium Hydroxide → 4-Chloro-3-isobutyl-but-3-en-2-one

HRID 1676106Notes

Reaction equation

HRID 1676106 reaction equation
O[CH:2]=[C:3]([CH2:7][CH:8]([CH3:10])[CH3:9])[C:4](=[O:6])[CH3:5].C(Cl)(=O)C([Cl:14])=O.[OH-].[Na+]>C(Cl)(Cl)Cl>[Cl:14][CH:2]=[C:3]([CH2:7][CH:8]([CH3:10])[CH3:9])[C:4](=[O:6])[CH3:5]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 65578Oxalyl chlorideHCID 866457654-Hydroxy-3-isobutyl-but-3-en-2-one

Product 1

HCID 866457664-Chloro-3-isobutyl-but-3-en-2-oneYield 99.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of 4-hydroxy-3-isobutyl-but-3-en-2-one (28 g, 197 mmol) in chloroform (350 mL) a soution of oxalylchloride (44.3 g, 349 mmol) in chloroform (50 mL) is added slowly during 5 min. The resulting dark brown mixture is stirred at rt for 2 h before it is cooled to 0° C. and treated with ice (100 g) followed by 1 N aq. NaOH (100 mL). When the quite violent gas evolution ceases the phases are separated (the still acidic aq. phase is discarded). The organic phase is washed with 1N aq. NaOH (3×75 mL) and 1 N aq. NaH2PO4 (75 mL), dried (MgSO4), filtered and evaporated to give crude 4-chloro-3-isobutyl-but-3-en-2-one (31.6 g) as a dark brown oil; LC-MS: tR=0.97 min.

Workup

  1. temperatureis cooled to 0° C.
  2. customare separated (the still acidic aq. phase
  3. washThe organic phase is washed with 1N 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-04b7007b60aa4fd7966a7dbb7468942c
Source dataset
uspto-grants-2011_08
Patent number
US08003800B2

Reaction notes

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