Ethyl Acetate → HCID 11043594, compound

HRID 650318Notes

Reaction equation

HRID 650318 reaction equation
C[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]([C:15]([O-:17])=[O:16])[CH2:10][CH2:11][C:12](=O)[CH:13]=2)=[CH:4][CH:3]=1.C(Cl)(=O)C([Cl:21])=O.CCO[C:27]([CH3:29])=O>C1(C)C=CC=CC=1>[Cl:21][C:12]1[CH:13]=[C:8]([C:5]2[CH:4]=[CH:3][CH:2]=[CH:7][CH:6]=2)[CH:9]([C:15]([O:17][CH2:27][CH3:29])=[O:16])[CH2:10][CH:11]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 65578Oxalyl chlorideHCID 86583682HCID 86583682, compound

Product 1

HCID 11043594HCID 11043594, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of 2-(4-methylphenyl)-4-oxocyclohex-2-enecarboxylate(1.24 g, 5.1 mmol) in toluene(10 ml) was added oxalyl chloride(2.58 g, 20.4 mmol). After stirring for 2 hr. at 70-75° C., AcOEt was added to the reaction mixture and washed with water, sat.NaHCO3 and brine, dried over MgSO4. Concentration afford 1.24 g of ethyl 4-chloro-2-phenylcyclohexa-2,4-dienecarboxylate and ethyl 4-chloro-2-phenylcyclohexa-3-dienecarboxylate(y=93.0%) as a pale yellow oil. This product was used at next step without purification. 1H-NMR(ppm, 300 MHz, CDCl3) δ 7.25-7.45(8H), 7.13-7.16(2H), 6.35(1H, s), 6.19(1H, s), 5.87(1H, brs), 4.09(2H, q, J=7.3 Hz), 3.93(2H, q, J=7.3 Hz), 3.64(1H, dd, J=3.8 and 8.6 Hz), 2.90-3.05(1H, m), 2.60-2.85(5H), 1.34(3H, t, J=7.3 Hz), 0.89(3H, t, J=7.3 Hz)

Workup

  1. washwashed with water
  2. dry with materialNaHCO3 and brine, dried over MgSO4
  3. concentrationConcentration

Sources & evidence

ORD record
ord-eec4c4609a3b4cfa8427669c06b51a84
Source dataset
uspto-grants-2001_08
Patent number
US06271418B1

Reaction notes

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