Phenol → HCID 14477521, compound

HRID 1639164Notes

Reaction equation

HRID 1639164 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O=[C:9]([CH2:23][CH2:24][C:25]([O-:27])=[O:26])[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=1)=[O:11].C1CCC(N=C=NC2CCCCC2)CC1>ClCCl>[O:7]([C:9]1([C:10]([O:12][CH2:13][C:14]2[CH:15]=[CH:16][C:17]([N+:20]([O-:22])=[O:21])=[CH:18][CH:19]=2)=[O:11])[CH2:23][CH2:24][C:25](=[O:26])[O:27]1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 10868DicyclohexylcarbodiimideHCID 221664155-[(4-Nitrophenyl)methoxy]-4,5-dioxopentanoate

Product 1

HCID 14477521HCID 14477521, compoundYield 43.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Phenol (941 mg), 1-(4-nitrobenzyl) 2-oxoglutarate (3.09 g) and DCC (2.27 g) were dissolved in 100 ml of dichloromethane and stirred for 3 hours at room temperature. The precipitated crystals were filtered off and the filtrate was subjected to silica gel column chromatography eluting with dichloromethane-ethyl acetate (3:1) to obtain 1.55 g of the title compound.

Workup

  1. filtrationThe precipitated crystals were filtered off
  2. washeluting with dichloromethane-ethyl acetate (3:1)

Sources & evidence

ORD record
ord-63700a705c5d439997273daf80ffc2f5
Source dataset
uspto-grants-1989_11
Patent number
US04882434

Reaction notes

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