Hydrochloric Acid → 2-Chloro-4-isopropylbenzoic acid

HRID 60563Notes

Reaction equation

HRID 60563 reaction equation
C[O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH3:12])[CH3:11])=[CH:6][C:5]=1[Cl:13].[OH-].[Na+].Cl>C1COCC1>[Cl:13][C:5]1[CH:6]=[C:7]([CH:10]([CH3:12])[CH3:11])[CH:8]=[CH:9][C:4]=1[C:3]([OH:14])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 669275682-Chloro-4-isopropyl-benzoic acid methyl ester

Product 1

HCID 198202302-Chloro-4-isopropylbenzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To solution of 2-chloro-4-isopropyl-benzoic acid methyl ester (68 mg, 0.33 mmol) in THF (3 ml) was added 2M NaOH (3 ml). The solution was heated to 70° C. for 1 hour. The reaction was cooled back to room temperature and brought to a pH of ˜3 with 1M HCl. The aqueous solution was extracted with EtOAc (3×). The combined organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated down under reduced pressure to give 2-chloro-4-isopropyl-benzoic acid as a yellow solid. Amount obtained: 62.7 mg (96%). 1H NMR (Chloroform-d) δ: 1.28 (d, J=6.8 Hz, 6 H) 2.95 (m, J=14.0, 6.9, 6.9 Hz, 1 H) 7.22 (dd, J=8.1, 1.7 Hz, 1 H) 7.36 (d, J=1.6 Hz, 1 H) 7.99 (d, J=8.2 Hz, 1 H).

Workup

  1. temperatureThe reaction was cooled back to room temperature
  2. extractionThe aqueous solution was extracted with EtOAc (3×)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated down under reduced pressure

Sources & evidence

ORD record
ord-fa6e3d69035e44f5bc57ced4a9f42368
Source dataset
uspto-grants-2016_09
Patent number
US09440994B2

Reaction notes

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