Hydrochloric Acid → 4-(4-ISOPROPYLPHENYL)BUTANOIC ACID

HRID 1892092Notes

Reaction equation

HRID 1892092 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10](=O)[CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].O.NN.[OH-].[K+].Cl>O>[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[CH:6][CH:5]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 96145Benzenebutanoic acid, 4-(1-methylethyl)-gamma-oxo-

Product 1

HCID 3476744-(4-ISOPROPYLPHENYL)BUTANOIC ACIDYield 58.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
127 °C

Procedure

A solution of compound 76 (0.5 g, 2.27 mmol) and 2 mL of 80% hydrazine hydrate was stirred at 45° C. for 1 hour. To the mixture, KOH (1 g, 17.8 mmol) was added and the reaction mixture was heated to 104-150° C. for 2 hours. After cooling to ambient temperature, the reaction mixture was diluted with 10 mL of water and acidified to pH 2 with aqueous HCl (1 M) and extracted with ethyl acetate (2×20 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica-gel (2×15 cm, petroleum ether:ethyl acetate=8:1 elution) to give 275 mg of compound 77. MS m/z 207 (M+H)+.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. extractionextracted with ethyl acetate (2×20 mL)
  3. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash column chromatography on silica-gel (2×15 cm, petroleum ether:ethyl acetate=8:1 elution)

Sources & evidence

ORD record
ord-929ff638949f4427be462e707a860e8f
Source dataset
uspto-grants-2013_08
Patent number
US08507647B2

Reaction notes

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