Methanol → Methyl 4-chloro-3,5-dinitrobenzoate

HRID 1595691Notes

Reaction equation

HRID 1595691 reaction equation
O=S(Cl)Cl.[N+:5]([C:8]1[CH:9]=[C:10]([CH:14]=[C:15]([N+:18]([O-:20])=[O:19])[C:16]=1[Cl:17])[C:11]([OH:13])=[O:12])([O-:7])=[O:6].[CH3:21]O>>[Cl:17][C:16]1[C:15]([N+:18]([O-:20])=[O:19])=[CH:14][C:10]([C:11]([O:13][CH3:21])=[O:12])=[CH:9][C:8]=1[N+:5]([O-:7])=[O:6]

Participants

4

Reactant 3

HCID 887Methanol2×HCID 83774-Chloro-3,5-dinitrobenzoic acidHCID 24386Thionyl Chloride

Product 1

HCID 96161Methyl 4-chloro-3,5-dinitrobenzoate

Procedure

2.96 ml of SOCl2 is added at 0° C., under an inert atmosphere and dropwise to 10 g of 3,5-dinitro-4-chloro-benzoic acid (JANSSEN) in 150 ml of methanol and agitation is carried out under reflux of methanol for 2 hours then for 15 hours at ambient temperature. The reaction medium is poured into ice and precipitation of the product is observed. After drying, 10.3 g of expected product is obtained.

Workup

  1. additionThe reaction medium is poured into ice and precipitation of the product
  2. customAfter drying

Sources & evidence

ORD record
ord-c83f1665e9284cf1bcabb2573bc11480
Source dataset
uspto-grants-2001_09
Patent number
US06288126B1

Reaction notes

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