HCID 57444533, compound → 1-(3-Chlorophenyl)butane-1,3-dione

HRID 860420Notes

Reaction equation

HRID 860420 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=1)[C:5]([CH:7]([C:15](=[O:17])[CH3:16])C(OC(C)(C)C)=O)=[O:6]>FC(F)(F)C(O)=O>[Cl:1][C:2]1[CH:3]=[C:4]([C:5](=[O:6])[CH2:7][C:15](=[O:17])[CH3:16])[CH:18]=[CH:19][CH:20]=1

Participants

3

Reactant 1

HCID 57444533HCID 57444533, compound

Product 1

HCID 152569661-(3-Chlorophenyl)butane-1,3-dioneYield 91.2%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of tert-butyl 2-(3-chlorobenzoyl)-3-oxobutanoate (8.82 g) in trifluoroacetic acid (40 mL) was stirred for 1 hour under an ice-bath. The volatile was removed in vacuo, and the residue was partitioned between ethyl acetate (150 mL) and saturated sodium bicarbonate. The organic layer was washed with brine, dried over magnesium sulfate, and evaporated to give 1-(3-chlorophenyl)-1,3-butanedione as a pale orange crystal (5.33 g).

Workup

  1. customThe volatile was removed in vacuo
  2. customthe residue was partitioned between ethyl acetate (150 mL) and saturated sodium bicarbonate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-d71c73545a8c487a8ff1d0de3606b43d
Source dataset
uspto-grants-2006_12
Patent number
US07153854B2

Reaction notes

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