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

HRID 446048Notes

Reaction equation

HRID 446048 reaction equation
[CH:1]1([C:4](=[O:21])[C:5]2[CH:10]=[CH:9][C:8]([C:11]([CH3:20])([CH3:19])[C:12]3[O:13]CC(C)(C)N=3)=[CH:7][CH:6]=2)[CH2:3][CH2:2]1.[ClH:22].[O:23]1CCOCC1>>[Cl:22][CH2:2][CH2:3][CH2:1][C:4]([C:5]1[CH:10]=[CH:9][C:8]([C:11]([CH3:20])([CH3:19])[C:12]([OH:23])=[O:13])=[CH:7][CH:6]=1)=[O:21]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 24720860HCID 24720860, compound

Product 1

HCID 109235672-(4-(4-Chlorobutanoyl)phenyl)-2-methylpropanoic acidYield 68%

Procedure

A mixture of 4-(cyclopropyl-oxo-methyl)-α,α-dimethyl-α-(4,4-dimethyloxazolin-2-yl)toluene, prepared according to Example 3, (42 g, 0.15 mole), 150 mL concentrated hydrochloric acid, and 150 mL 1,4-dioxane was brought to reflux for 18 hours. The mixture was extracted three times with ethyl acetate. The organics were washed with saturated NaCl solution, dried over MgSO4, and concentrated. Crude product was purified by column chromatography using 240 g silica gel, and eluting with 81:14:5 hexanes/ethyl acetate/acetic acid. Cleaner fractions were combined and recrystallized from methylene chloride/hexanes to afford 27 g of 4-(4-chloro-1-oxobutyl)-α,α-dimethylphenylacetic acid as a white solid (68%).

Workup

  1. customprepared
  2. temperatureto reflux for 18 hours
  3. extractionThe mixture was extracted three times with ethyl acetate
  4. washThe organics were washed with saturated NaCl solution
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customCrude product was purified by column chromatography
  8. washeluting with 81:14:5 hexanes/ethyl acetate/acetic acid
  9. customrecrystallized from methylene chloride/hexanes

Sources & evidence

ORD record
ord-7ac3eca103924e47a5a2c62888c2da8e
Source dataset
uspto-grants-2013_07
Patent number
US08476445B2

Reaction notes

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