Hydrochloric Acid → 1,3-Benzenediol, 2-chloro-4,6-dinitro-

HRID 1609378Notes

Reaction equation

HRID 1609378 reaction equation
[Cl:1][C:2]1[C:7](Cl)=[C:6]([N+:9]([O-:11])=[O:10])[CH:5]=[C:4]([N+:12]([O-:14])=[O:13])[C:3]=1[OH:15].CC(C)([O-:19])C.[K+].[OH-].[K+].Cl>O.CN1C(=O)CCC1>[Cl:1][C:2]1[C:7]([OH:19])=[C:6]([N+:9]([O-:11])=[O:10])[CH:5]=[C:4]([N+:12]([O-:14])=[O:13])[C:3]=1[OH:15]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 108579782,3-Dichloro-4,6-dinitrophenolHCID 23665647Potassium tert-butoxide

Product 1

HCID 111072901,3-Benzenediol, 2-chloro-4,6-dinitro-Yield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
85 °C

Procedure

A solution of 2,3-dichloro-4,6-dinitrophenol (2.2 g, 0,008 mol, from previous example), 4.5 g of potassium t-butoxide, 0.4 g of potassium hydroxide, 30 mL of N-methyl pyrrolidinone, and 15 mL of water in a 100 mL round-bottomed flask with stir bar is heated to 85° C. for 6 hours. Upon completion, the reaction mixture is poured into 50 mL of aqueous hydrochloric acid. The resulting product is isolated by filtration, washed with cold water, and air dried. The product is recrystallized from a minimal amount of methanol to yield 1.97 g of 2-chloro-4,6-dinitroresorcinol (95% yield) (85% overall from 1,2-dichloro-3,5-dinitrobenzene).

Workup

  1. customThe resulting product is isolated by filtration
  2. washwashed with cold water, and air
  3. customdried
  4. customThe product is recrystallized from a minimal amount of methanol

Sources & evidence

ORD record
ord-5b3d6a07582e4fee91bc8002b06e4fc7
Source dataset
uspto-grants-1995_03
Patent number
US05399768

Reaction notes

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