Sulfuric Acid → 1-Chloro-4-nitro-9H-xanthen-9-one

HRID 364161Notes

Reaction equation

HRID 364161 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:18]([O-:20])=[O:19])=[C:6]([CH:17]=1)[O:7][C:8]1[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10]([OH:12])=O.S(=O)(=O)(O)O.C(Cl)(Cl)Cl>O>[Cl:1][C:2]1[C:17]2[C:10](=[O:12])[C:9]3[C:8](=[CH:16][CH:15]=[CH:14][CH:13]=3)[O:7][C:6]=2[C:5]([N+:18]([O-:20])=[O:19])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 6212ChloroformHCID 13689005HCID 13689005, compound

Product 1

HCID 136890061-Chloro-4-nitro-9H-xanthen-9-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The 1-chloro-4-nitro-9H-xanthen-9-one was prepared as follows: Crude 2-(5'-chloro-2-nitrophenoxy)-benzoic acid (50 g) was added to 200 g of concentrated sulfuric acid. The mixture was held at 75° C. for 4.5 hours, and added to a stirred mixture of 1.5 1 of chloroform and water containing ice as needed to maintain the temperature below 35° C. The chloroform layer was separated, washed with 5% sodium bicarbonate, evaporated to dryness and the residue was crystallized from 200 ml of toluene and 30 ml of cyclohexane to provide the product mp 175°-186° C.

Workup

  1. additioncontaining ice
  2. temperatureto maintain the temperature below 35° C
  3. customThe chloroform layer was separated
  4. washwashed with 5% sodium bicarbonate
  5. customevaporated to dryness
  6. customthe residue was crystallized from 200 ml of toluene and 30 ml of cyclohexane

Sources & evidence

ORD record
ord-8822305e0c4d40c09230683967535054
Source dataset
uspto-grants-1986_08
Patent number
US04604390

Reaction notes

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