Hydrochloric Acid → HCID 57843569, compound

HRID 734278Notes

Reaction equation

HRID 734278 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4]([C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[CH:13]=1)([CH3:11])[CH2:5][CH:6](OC)[O:7]C.Cl>C1COCC1.O>[CH3:1][O:2][C:3](=[O:20])[C:4]([C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[CH:13]=1)([CH3:11])[CH2:5][CH:6]=[O:7]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 57843543HCID 57843543, compound

Product 1

HCID 57843569HCID 57843569, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 6 g (19 mmol) 2-(3,4-dichloro-phenyl)-4,4-dimethoxy-2-methyl-butyric acid methyl ester and 28 mL 2N HCl aq. in 60 mL THF and 60 mL water was stirred at room temperature for 20 h. The mixture was extracted with diethyl ether. The combined organic phases were washed with sat. NaCl aq., dried with Na2SO4 and evaporated to dryness. The residue was subjected to column chromatography on silica eluting with a gradient formed from ethyl acetate and hexane. The product containing fractions were evaporated to yield 3 g (58%) of the title compound as light yellow oil.

Workup

  1. extractionThe mixture was extracted with diethyl ether
  2. washThe combined organic phases were washed with sat. NaCl aq.
  3. dry with materialdried with Na2SO4
  4. customevaporated to dryness
  5. customformed from ethyl acetate and hexane
  6. additionThe product containing fractions
  7. customwere evaporated

Sources & evidence

ORD record
ord-c6d03caadc334f3eb9e7b4893142aa8e
Source dataset
uspto-grants-2009_09
Patent number
US07592345B2

Reaction notes

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