4-Nitrophenol → HCID 14347606, compound

HRID 1651117Notes

Reaction equation

HRID 1651117 reaction equation
[C:1]1([C:7]2([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:9][C@H:8]2[CH2:10][CH2:11][C:12]([OH:14])=[O:13])[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:13][C:12](=[O:14])[CH2:11][CH2:10][C@@H:8]2[CH2:9][C:7]2([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 14347597HCID 14347597, compound

Product 1

HCID 14347606HCID 14347606, compoundYield 72.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
30 °C

Procedure

As in Example 111, (R)-2,2-diphenylcyclopropanepropanoic acid (6.1 g) and 4-nitrophenol (3,8 g) in dichloromethane (100 mL) was treated with 1,3-dicyclohexylcarbodiimide (4.7 g) and the mixture was stirred at 30° C. for 1 hour. The product obtained from the usual work up was crystallized from 2-propanol to yield 6.4 g of (R)-2,2-diphenylcyclopropanepropanoic acid 4-nitrophenyl ester, mp 77.5°-76.5° C.; [α]D25 +93.7° (c, 1.0, MeOH)

Workup

  1. customThe product obtained from the usual work
  2. customup was crystallized from 2-propanol

Sources & evidence

ORD record
ord-8006adda4f0e4f49a25ec5c3633fd935
Source dataset
uspto-grants-1990_05
Patent number
US04927826

Reaction notes

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