Hydrochloric Acid → HCID 9965078, compound

HRID 650319Notes

Reaction equation

HRID 650319 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:6][CH:7]=1.ClC1CCC(C(OCC)=O)=C(C2C=CC=CC=2)C=1.C(O[K])(C)(C)C.Cl>C(O)(C)(C)C.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10967324HCID 10967324, compoundHCID 11043594HCID 11043594, compoundHCID 178418922HCID 178418922, compound

Product 1

HCID 9965078HCID 9965078, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

To a stirred solution of ethyl 4-chloro-2-phenylcyclohexa-2,4-dienecarboxylate and ethyl 4-chloro-2-phenylcyclohexa-1,3-dienecarboxylate(200 mg, 0.762 mmol) in tert-BuOH(3 ml), tert-BuOK(103 mg, 0.914 mmol) was added by portion on a water bath. After stirring for 2 days, water was added to the reaction mixture and it was acidified with dil. HCl aq., extracted with AcOEt. The organic layer was washed with brine and dried over MgSO4. Concentration of the organic layer afford a mixture(200 mg) of ethyl 4-chloro-2-phenylbenzoate and 4-chloro-2-phenylbenzoic acid. 1H-NMR(ppm, 300 MHz, CDCl3) δ ester 7.79(1H, d, J=8.0 Hz), 7.10-7.50(7H), 4.07(2H, d, J=6.9 Hz), 0.98(3H, t, J=6.9 Hz); acid 7.91(1H, d, J=8.7 Hz)

Workup

  1. extractionextracted with AcOEt
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-c425338989ff47e5acc0c8d05ccea5b9
Source dataset
uspto-grants-2001_08
Patent number
US06271418B1

Reaction notes

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