Dichloromethane → HCID 11160042, compound

HRID 850328Notes

Reaction equation

HRID 850328 reaction equation
COC1C=CC(C[O:8][CH2:9][CH2:10][C:11]([CH2:13][O:14][C:15](=[O:22])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH2:12])=CC=1.C(Cl)Cl.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>O>[OH:8][CH2:9][CH2:10][C:11]([CH2:13][O:14][C:15](=[O:22])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[CH2:12]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 19363554HCID 19363554, compound

Product 1

HCID 11160042HCID 11160042, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Combine 4-(p-methoxybenzyloxy)-2-benzoyloxymethylbut-1-ene (1.08 g, 3.30 mmol) with methylene chloride (10 mL) and water (0.5 mL) and stir rapidly. Add 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (0.826 gm, 3.64 mmol). After 0.25 hours filter the reaction mixture and rinse the filter cake with methylene chloride (20 mL) and concentrate the filtrate in vacuo. Chromatograph on silica gel eluting with 1/9 ethyl acetate/hexane to give the title compound as an oil. Rf =0.28; silica gel, 1/9 ethyl acetate/hexane.

Workup

  1. filtrationAfter 0.25 hours filter the reaction mixture
  2. washrinse the filter cake with methylene chloride (20 mL)
  3. concentrationconcentrate the filtrate in vacuo

Sources & evidence

ORD record
ord-e8341c2256e64540935d4c105d63b1fd
Source dataset
uspto-grants-2000_01
Patent number
US06017923

Reaction notes

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