4-Nitrophenol → HCID 14347462, compound

HRID 1110611Notes

Reaction equation

HRID 1110611 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](/[C:9](/[CH2:16][CH2:17][CH2:18][CH3:19])=[CH:10]/[CH:11]=[CH:12]/[C:13]([OH:15])=[O:14])=[CH:5][CH:4]=1.[N+:20]([C:23]1[CH:28]=[CH:27][C:26](O)=[CH:25][CH:24]=1)([O-:22])=[O:21].C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[N+:20]([C:23]1[CH:28]=[CH:27][C:26]([O:14][C:13](=[O:15])/[CH:12]=[CH:11]/[CH:10]=[C:9](/[C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)\[CH2:16][CH2:17][CH2:18][CH3:19])=[CH:25][CH:24]=1)([O-:22])=[O:21]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 10868DicyclohexylcarbodiimideHCID 14347293HCID 14347293, compound

Product 1

HCID 14347462HCID 14347462, compoundYield 77.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

As in Example 11, (E,E)-5-(4-methoxyphenyl)-2,4-nonadienoic acid (3.12 g) and 4-nitrophenol (2 g) in 20 mL of dichloromethane was treated with 1,3-dicyclohexylcarbodiimide (2,49 g) and the mix(ure was stlrred at room temperature for 3 days. After the normal work up, crystallization of the crude product from 2-propanol yielded 3.55 g of (E,E)-5-(4-methoxyphenyl)-2,4-nonadienoic acid 4-nitrophenyl ester, mp 78°-80° C., resolidified and remelted at 115° C.

Workup

  1. customAfter the normal work up, crystallization of the crude product from 2-propanol

Sources & evidence

ORD record
ord-7aeb2921a43d4968819e43ba3ca34b9b
Source dataset
uspto-grants-1990_12
Patent number
US04975438

Reaction notes

Loading…