Hydrochloric Acid → HCID 67040724, compound

HRID 605094Notes

Reaction equation

HRID 605094 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].Cl[C:19]1[CH:27]=[CH:26][C:22]([C:23]([OH:25])=[O:24])=[CH:21][C:20]=1[N+:28]([O-:30])=[O:29].Cl>CS(C)=O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][C:19]2[CH:27]=[CH:26][C:22]([C:23]([OH:25])=[O:24])=[CH:21][C:20]=2[N+:28]([O-:30])=[O:29])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 73204-Chloro-3-nitrobenzoic acidHCID 7638MonobenzoneHCID 14797Potassium Hydroxide

Product 1

HCID 67040724HCID 67040724, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A solution of 4-Benzyloxy-phenol (2.00 g, 0.01 mol) and potassium hydroxide (1.12 g, 0.02 mol) in anhydrous dimethylsulfoxide (20 mL) was stirred at room temperature for 10 minutes under a nitrogen atmosphere. A solution of 4-chloro-3-nitrobenzoic acid (2.01 g, 0.01 mol) in dimethylsulfoxide (5 mL) was added and the mixture heated to 120° for 1 hour. The reaction was then cooled in an ice bath and poured into 100 mL of ice-water. The mixture was acidified with concentrated HCl to pH 3 then the resultant solid was colleted by vacuum filtration, washed with water and dried in a vacuum oven to provide the title product (3.5 g, 96%).

Workup

  1. temperaturethe mixture heated to 120° for 1 hour
  2. temperatureThe reaction was then cooled in an ice bath
  3. filtrationthe resultant solid was colleted by vacuum filtration
  4. washwashed with water
  5. customdried in a vacuum oven

Sources & evidence

ORD record
ord-f9dea7e55e614dd388ac5e251392a1df
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

Loading…