Hydrochloric Acid → 2-Chloro-4-ethenylbenzoic acid

HRID 60557Notes

Reaction equation

HRID 60557 reaction equation
C[O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[CH2:11])=[CH:6][C:5]=1[Cl:12].[OH-].[Na+].Cl>C1COCC1>[Cl:12][C:5]1[CH:6]=[C:7]([CH:10]=[CH2:11])[CH:8]=[CH:9][C:4]=1[C:3]([OH:13])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 57461224Methyl 2-chloro-4-vinylbenzoate

Product 1

HCID 583731462-Chloro-4-ethenylbenzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To solution of 2-chloro-4-vinyl-benzoic acid methyl ester (50 mg, 0.26 mmol) in THF (2 ml) was added 2M NaOH (1 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-vinyl benzoic acid as a white solid. Amount obtained: 40.3 mg (86%). LCMS (M/Z): 183 (M+H); 1H NMR (Chloroform-d) δ: 5.47 (d, J=10.9 Hz, 1 H) 5.93 (s, 1 H) 6.70 (dd, J=17.6, 10.9 Hz, 1 H) 7.38 (dd, J=8.2, 1.8 Hz, 1 H) 7.52 (s, 1 H) 8.02 (d, J=8.0 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-73729dead4a24803b2491e45a584eb3b
Source dataset
uspto-grants-2016_09
Patent number
US09440994B2

Reaction notes

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