Ethyl Acetate → HCID 11482466, compound

HRID 650321Notes

Reaction equation

HRID 650321 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 (10 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-7a32e925ca9a4b3d9e0acd8aeba96827
Source dataset
uspto-grants-2001_08
Patent number
US06271418B1

Reaction notes

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