2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 70225591, compound

HRID 1532862Notes

Reaction equation

HRID 1532862 reaction equation
[CH3:1][O:2][C:3](=[O:38])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][O:11][CH:12]([CH2:24][CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)[CH2:13][O:14]CC2C=CC(OC)=CC=2)=[CH:6][C:5]=1[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[CH3:37].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>ClCCl.O.CCOC(C)=O.CCCCCC>[CH:25]1([CH2:24][CH:12]([O:11][CH2:10][C:7]2[CH:8]=[CH:9][C:4]([C:3]([O:2][CH3:1])=[O:38])=[C:5]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[CH3:37])[CH:6]=2)[CH2:13][OH:14])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

6

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 72604112HCID 72604112, compound

Product 1

HCID 70225591HCID 70225591, compoundYield 90%

Reagents, catalysts & solvents 3

HCID 962WaterCatalystHCID 6344DichloromethaneSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

To a solution of N-[4-(3-cyclohexyl-1-(4-methoxybenzyloxy)prop-2-yloxymethyl)-2-(2-methylphenyl)benzoic acid methyl ester (Example 1051B, 360 mg) in dichloromethane (2 mL) was added water (5 drops), and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (190 mg). After 50 min, the reaction was diluted with EtOAc/hexane (1:1, 10 mL), dried (MgSO4), and filtered through a pad of silica gel. The filtrate was concentrated, and the residue was purified by silica gel chromatography eluting with 20%-30% EtOAc/hexane to give the title compound (230 mg, 90%) as a colorless oil.

Workup

  1. dry with materialdried (MgSO4)
  2. filtrationfiltered through a pad of silica gel
  3. concentrationThe filtrate was concentrated
  4. customthe residue was purified by silica gel chromatography
  5. washeluting with 20%-30% EtOAc/hexane

Sources & evidence

ORD record
ord-98d8e461878540e99ede1868a2777922
Source dataset
uspto-grants-2001_03
Patent number
US06204293B1

Reaction notes

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