Dichloromethane → HCID 19363562, compound

HRID 850327Notes

Reaction equation

HRID 850327 reaction equation
COC1C=CC(C[O:8][CH2:9][CH2:10]/[C:11](/[CH2:14][O:15][C:16](=[O:23])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:12]\[Cl:13])=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](/[CH2:14][O:15][C:16](=[O:23])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[CH:12]\[Cl:13]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 86755090HCID 86755090, compound

Product 1

HCID 19363562HCID 19363562, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Combine (E)-4-(p-methoxybenzyloxy)-2-benzoyloxymethyl-1-chlorobut-1-ene (1.02.6 g, 7.18 mmol) with methylene chloride (16 mL) and water (1 mL) and stir rapidly. Add 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (1.79 gm, 7.90 mmol). After 2 hours, filter the reaction mixture, rinse the filter cake with methylene chloride (200 mL) and concentrate the filtrate in vacuo. Chromatograph on silica gel eluting with 1/2 ethyl acetate/hexane to give the title compound as an oil. Rf =0.25; silica gel, 1/2 ethyl acetate/hexane.

Workup

  1. filtrationfilter the reaction mixture
  2. washrinse the filter cake with methylene chloride (200 mL)
  3. concentrationconcentrate the filtrate in vacuo

Sources & evidence

ORD record
ord-248bb7acfede44519a7d1e1505e2a61e
Source dataset
uspto-grants-2000_01
Patent number
US06017923

Reaction notes

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