Ethyl Acetate → HCID 11482466, compound

HRID 1251029Notes

Reaction equation

HRID 1251029 reaction equation
O[CH:2]1[CH2:7][CH2:6][CH: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.S(Cl)([Cl:21])=O.CCOC(C)=O>C1(C)C=CC=CC=1>[Cl:21][CH:2]1[CH2:7][CH2:6][CH: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

5

Reactant 3

HCID 8857Ethyl AcetateHCID 24386Thionyl ChlorideHCID 18325913HCID 18325913, compound

Product 1

HCID 11482466HCID 11482466, compoundYield 102.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of ethyl 4-hydroxy-2-phenylcyclohex-2-enecarboxylate (100 mg, 0.407 mmol) in toluene(2 ml) was added thionyl chloride(0.074 ml, 1.02 mmol) at 5° C. After stirring for 3 hr. at room temperature. AcOEt was added to the reaction mixture and it was washed with water, sat.NaHCO3 aq. and brine, dried over MgSO4. Concentration of the organic layer afford 110 mg of ethyl 4-chloro-2-phenylcyclohex-2-enecarboxylate(y=100%) as a pale yellow oil. 1H-NMR(ppm, 300 MHz, CDCl3) δ 7.25-7.37(5H, m), 6.27 and 6.18(1H, d and t, J=4.6 and 1.7 Hz), 4.87-4.91 and 4.74-4.79(1H, m), 4.03 and 3.96(2H, q, J=6.9 and 7.1 Hz), 3.68-3.76(1H, m), 2.05-2.37(4H, m), 1.09 and 0.97(3H, t, J=6.9 and 7.1 Hz).

Workup

  1. customat room temperature
  2. washwas washed with water
  3. dry with materialNaHCO3 aq. and brine, dried over MgSO4

Sources & evidence

ORD record
ord-abb48f4aabe24fa4903af89d7e825e52
Source dataset
uspto-grants-2002_01
Patent number
US06340772B1

Reaction notes

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