Hydrochloric Acid → 2,2-Bis-(4-mesyloxy-3-nitrophenyl)-hexafluoropropane

HRID 1086324Notes

Reaction equation

HRID 1086324 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([C:22]2[CH:27]=[CH:26][C:25]([OH:28])=[C:24]([N+:29]([O-:31])=[O:30])[CH:23]=2)([C:18]([F:21])([F:20])[F:19])[C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=1[N+:32]([O-:34])=[O:33].Cl>N1C=CC=CC=1>[S:2]([O:28][C:25]1[CH:26]=[CH:27][C:22]([C:13]([C:10]2[CH:11]=[CH:12][C:7]([O:6][S:2]([CH3:1])(=[O:4])=[O:3])=[C:8]([N+:32]([O-:34])=[O:33])[CH:9]=2)([C:18]([F:21])([F:19])[F:20])[C:14]([F:16])([F:15])[F:17])=[CH:23][C:24]=1[N+:29]([O-:31])=[O:30])([CH3:1])(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 31297Methanesulfonyl chlorideHCID 111336832,2-Bis(3-nitro-4-hydroxyphenyl)hexafluoropropane

Product 1

HCID 142050422,2-Bis-(4-mesyloxy-3-nitrophenyl)-hexafluoropropaneYield 85%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

11.5 g (0.1 mol) of methanesulfonyl chloride are added dropwise, at a reaction temperature of 0-5° C., to a mixture of 21.3 g (0.05 mol) of 2,2-bis-(4-hydroxy-3-nitrophenyl)-hexafluoropropane and 100 ml of pyridine. Stirring is continued for 1 hour at 5° C. and overnight at room temperature. The reaction mixture is then acidified, first with dilute hydrochloric and then with half-concentrated hydrochloric acid; the precipitate which is deposited is filtered off with suction and washed with water until neutral. The crude product (29.3 g) is then recrystallized from toluene, resulting in 24.8 g of analytically pure 2,2-bis-(4-mesyloxy-3-nitrophenyl)-hexafluoropropane to be isolated. Yield 85%; m.p. 119-121° C.

Workup

  1. additionfirst with dilute hydrochloric
  2. filtrationthe precipitate which is deposited is filtered off with suction
  3. washwashed with water until neutral
  4. customThe crude product (29.3 g) is then recrystallized from toluene

Sources & evidence

ORD record
ord-367d7b325d334add9a422dc99a56328d
Source dataset
uspto-grants-1991_07
Patent number
US05028728

Reaction notes

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