4-Nitrophenol → HCID 14347309, compound

HRID 1110516Notes

Reaction equation

HRID 1110516 reaction equation
[C:1]1([C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:8]/[CH:9]=[C:10](\[CH3:14])/[C:11]([OH:13])=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+:21]([C:24]1[CH:29]=[CH:28][C:27](O)=[CH:26][CH:25]=1)([O-:23])=[O:22].C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[N+:21]([C:24]1[CH:29]=[CH:28][C:27]([O:12][C:11](=[O:13])/[C:10](/[CH3:14])=[CH:9]/[CH:8]=[C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:26][CH:25]=1)([O-:23])=[O:22]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 10868DicyclohexylcarbodiimideHCID 14347308HCID 14347308, compound

Product 1

HCID 14347309HCID 14347309, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (E)-5,5-diphenyl-2-methyl-2,4-pentadienoic acid (1.85 g) and 4-nitrophenol (1.12 g) in dichloromethane (25 mL), stirred at 0°-5° C. in an ice-water bath, was treated with 1,3-dicyclohexylcarbodiimide (1.44 g). The mixture was stirred at 0°-5° C. for 30 minutes, then at room temperature for 1 hour. After the precipitated dicyclohexylurea was filtered off, the concentrated filtrate was passed through a short column of silica gel (~25 g) made up in dichloromethane-hexane (3:2). The appropriate fractions were combined and evaporated to give 2.4 g of (E)-5,5-diphenyl-2-methyl-2,4-pentadienoic acid 4-nitrophenyl ester. Crystallization of the material from 2-propanol furnished 1.64 g of (E)-5,5-diphenyl-2-methyl-2,4-pentadienoic acid 4-nitrophenyl ester mp 139°-141° C. Anal. Calculated for C24H19NO4 : C, 74.79; H, 4.97; N, 3.63 Found: C, 74.83; H, 5.05 ; N, 3.68.

Workup

  1. waitat room temperature for 1 hour
  2. filtrationAfter the precipitated dicyclohexylurea was filtered off
  3. customevaporated

Sources & evidence

ORD record
ord-d93b780ebc34480eaf9a1e9005cdf64b
Source dataset
uspto-grants-1990_12
Patent number
US04975438

Reaction notes

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