Hydrochloric Acid → HCID 54094141, compound

HRID 2256953Notes

Reaction equation

HRID 2256953 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=O)=[C:4]([S:12][CH3:13])[C:3]=1[CH3:14].[CH3:15][C:16]([CH:18]1[CH2:20][CH2:19]1)=[O:17].[H-].[Na+].Cl>O1CCCC1>[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6](=[O:8])[CH2:15][C:16]([CH:18]2[CH2:20][CH2:19]2)=[O:17])=[C:4]([S:12][CH3:13])[C:3]=1[CH3:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 13004Cyclopropyl methyl ketoneHCID 24758Sodium hydrideHCID 54088631HCID 54088631, compound

Product 1

HCID 54094141HCID 54094141, compoundYield 84.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of methyl 4-chloro-3-methyl-2-(methylsulphenyl)benzoate (19.5 g) and cyclopropyl methyl ketone (13.4 g) in dry tetrahydrofuran was added to a stirred heated suspension of sodium hydride (80% oil dispersion, 4.8 g) in dry tetrahydrofuran. The mixture was stirred and heated at reflux for 2 hours. It was cooled and hydrochloric acid (2 ml) was added. The layers were separated and the aqueous layer was extracted with ether. The combined organic layers were washed with water, saturated aqueous sodium bicarbonate, water, dried (Na2SO4) and filtered. The filtrate was evaporated to dryness to give 1-(4-chloro-3-methyl-2-methylsulphenylphenyl)-3-cyclopropylpropan-1,3-dione (20.19 g) as a yellow oil, NMR(CDCl3) 0.9(m,2H), 1.2 (m,2H), 1.7(m, 1H), 2.3(s,3H), 2.65(s,3H), 5.85 (s, 1H), 7. 15(d, 1H), 7.3(d, 1H), 15.7-16.0(bs, 1H).

Workup

  1. additionwas added to a stirred
  2. temperatureheated
  3. temperatureheated
  4. temperatureat reflux for 2 hours
  5. temperatureIt was cooled
  6. customThe layers were separated
  7. extractionthe aqueous layer was extracted with ether
  8. washThe combined organic layers were washed with water, saturated aqueous sodium bicarbonate, water
  9. dry with materialdried (Na2SO4)
  10. filtrationfiltered
  11. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-cacc651084144710807e11b7afa5daf1
Source dataset
uspto-grants-1997_08
Patent number
US05656573

Reaction notes

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