Hydrochloric Acid → 2-(4-(4-Chlorobutanoyl)phenyl)-2-methylpropanoic acid

HRID 1279744Notes

Reaction equation

HRID 1279744 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]([CH3:22])([CH3:21])[C:14]2[O:15]CC(C)(C)N=2)=[CH:9][CH:8]=1)=[O:6].Cl.[O:24]1CCOCC1>>[Cl:1][CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:8]=[CH:9][C:10]([C:13]([CH3:22])([CH3:21])[C:14]([OH:15])=[O:24])=[CH:11][CH:12]=1)=[O:6]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 15512391HCID 15512391, compound

Product 1

HCID 109235672-(4-(4-Chlorobutanoyl)phenyl)-2-methylpropanoic acid

Procedure

A mixture of 4-(4-chloro-1-oxobutyl)-α,α-dimethyl-α-(4,4-dimethyloxazolin-2-yl)toluene, prepared according to Example 3, (47.8 g, 0.15 mole), 150 mL concentrated hydrochloric acid, and 150 mL 1,4-dioxane is brought to reflux for 18 hours. The mixture is extracted three times with ethyl acetate. The organics are washed with saturated NaCl solution, dried over MgSO4, and concentrated. Crude product is purified by column chromatography using silica gel, and eluting with hexane/ethyl acetate/acetic acid. Cleaner fractions are combined and recrystallized from methylene chloride/hexanes to afford 4-(4-chloro-1-oxobutyl)-α,α-dimethylphenylacetic acid.

Workup

  1. customprepared
  2. temperatureto reflux for 18 hours
  3. extractionThe mixture is extracted three times with ethyl acetate
  4. washThe organics are washed with saturated NaCl solution
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customCrude product is purified by column chromatography
  8. washeluting with hexane/ethyl acetate/acetic acid
  9. customrecrystallized from methylene chloride/hexanes

Sources & evidence

ORD record
ord-ae994ef6d4b84c09b61bc9363a0324cc
Source dataset
uspto-grants-2002_09
Patent number
US06448406B1

Reaction notes

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