Hydrochloric Acid → 1-Cyclopropyl-3-phenylpropane-1,3-dione

HRID 1857081Notes

Reaction equation

HRID 1857081 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].C[O:11][C:12]([CH:14]1[CH2:16][CH2:15]1)=O.C[O-].[Na+].Cl>CS(C)=O.CCCCCCC>[C:4]1([C:1](=[O:3])[CH2:2][C:12]([CH:14]2[CH2:16][CH2:15]2)=[O:11])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7410AcetophenoneHCID 76122Methyl cyclopropanecarboxylateHCID 10942334Sodium Methoxide

Product 1

HCID 232819771-Cyclopropyl-3-phenylpropane-1,3-dioneYield 86%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8900HeptaneSolvent

Conditions

Temperature
40 °C

Procedure

Acetophenone (10.1 g; 0.084 mol) and MCPC (25.2 g; 0.25 mol; 3 equiv) were dissolved in DMSO (46.1 g). Sodium methoxide (9.1 g; 0.168 mol; 2.0 equiv) was added slowly while maintaining the temperature below 30° C. The reaction mixture was then heated to 40° C. for 5 h. Heptane (100 mL) was added followed by sufficient 20% aqueous HCl such that the pH was less than 5. The mixture was stirred for 15 min and then allowed to settle. The lower aqueous layer was decanted and discarded. The upper organic layer was washed with 40 mL of water, and the solvent was stripped to afford 14 g of crude 8, which was 97.2% pure by GC (area %) to afford an 86% yield of 8.

Workup

  1. temperaturewhile maintaining the temperature below 30° C
  2. customThe lower aqueous layer was decanted
  3. washThe upper organic layer was washed with 40 mL of water
  4. customto afford 14 g of crude 8, which

Sources & evidence

ORD record
ord-00dca6f4e8b04d449699eccb62b69a8b
Source dataset
uspto-grants-2000_11
Patent number
US06143935

Reaction notes

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