2-Chloro-4-methoxyphenol → Methyl 3,5-dinitro-4-(2'-chloro-4'-methoxyphenoxy)benzoate

HRID 1598348Notes

Reaction equation

HRID 1598348 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[OH:10].ClC1C=C(OC)C=CC=1[O-].[K+].Cl[C:23]1[C:32]([N+:33]([O-:35])=[O:34])=[CH:31][C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:25][C:24]=1[N+:36]([O-:38])=[O:37]>C(O)C>[N+:33]([C:32]1[CH:31]=[C:26]([CH:25]=[C:24]([N+:36]([O-:38])=[O:37])[C:23]=1[O:10][C:3]1[CH:4]=[CH:5][C:6]([O:8][CH3:9])=[CH:7][C:2]=1[Cl:1])[C:27]([O:29][CH3:30])=[O:28])([O-:35])=[O:34]

Participants

5

Reactant 3

HCID 874592-Chloro-4-methoxyphenolHCID 96161Methyl 4-chloro-3,5-dinitrobenzoateHCID 23716091Potassium 2-chloro-4-methoxyphenolate

Product 1

HCID 18349326Methyl 3,5-dinitro-4-(2'-chloro-4'-methoxyphenoxy)benzoateYield 66%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The dinitro precursor was prepared by reacting 2-chloro-4-methoxyphenol (Aldrich Chemical Co., Milwaukee, Wis.) as the potassium 2-chloro-4-methoxyphenolate with methyl 4-chloro-3,5-dinitrobenzoate, as described in Example 1.2.1. The methyl 3,5-dinitro-4-(2'-chloro-4'-methoxyphenoxy)benzoate product (66% yield) was crystallized from ethanol to give orange crystals. Melting point: 116°-119° C.

Sources & evidence

ORD record
ord-b7823c37ff8c444d9373864ca58fd723
Source dataset
uspto-grants-1998_04
Patent number
US05736576

Reaction notes

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