Diethyl Ether → HCID 178427636, compound

HRID 1613526Notes

Reaction equation

HRID 1613526 reaction equation
[CH:1]1([Ti:6]([CH:29]2[CH:33]=[CH:32][CH:31]=[CH:30]2)([C:18]2[C:23]([F:24])=[C:22]([F:25])[C:21]([OH:26])=[C:20]([F:27])[C:19]=2[F:28])[C:7]2[C:12]([F:13])=[C:11]([F:14])[C:10]([OH:15])=[C:9]([F:16])[C:8]=2[F:17])[CH:5]=[CH:4][CH:3]=[CH:2]1.[C:34]1([CH3:44])[CH:39]=[CH:38][C:37]([S:40](Cl)(=[O:42])=[O:41])=[CH:36][CH:35]=1.[OH-:45].[Na+].CCO[CH2:50][CH3:51]>C1(C)C=CC=CC=1>[CH:29]1([Ti:6]([CH:1]2[CH:5]=[CH:4][CH:3]=[CH:2]2)([C:18]2[C:23]([F:24])=[C:22]([F:25])[C:21]([O:26][S:40]([C:37]3[CH:38]=[CH:39][C:50]([CH3:51])=[CH:35][CH:36]=3)(=[O:41])=[O:45])=[C:20]([F:27])[C:19]=2[F:28])[C:7]2[C:12]([F:13])=[C:11]([F:14])[C:10]([O:15][S:40]([C:37]3[CH:38]=[CH:39][C:34]([CH3:44])=[CH:35][CH:36]=3)(=[O:42])=[O:41])=[C:9]([F:16])[C:8]=2[F:17])[CH:33]=[CH:32][CH:31]=[CH:30]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 178516669HCID 178516669, compound

Product 1

HCID 178427636HCID 178427636, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
40 °C

Procedure

5.1 g (0.010 mol) of bis(cyclopentadienyl)bis(2,3,5,6-tetrafluoro-4-hydroxyphenyl)titanium are suspended in 100 ml of toluene in a sulfation flask under nitrogen as protective gas. 5.7 g (0.030 mol) of toluene-4-sulfonyl chloride are then added. 40 ml of 1N sodium hydroxide solution (0.040 mol) are subsequently added dropwise, and the mixture is stirred for 4 hours at 40° C. After a check of the reaction using thin-layer chromatography, the reaction mixture is allowed to cool. 100 ml of ice-water and 100 ml of ether are then added. The organic phase is separated off and washed several times with a little water until the reaction on pH paper is neutral. The organic phase is dried using magnesium sulfate and evaporated on a vacuum rotary evaporator. An orange-red crystalline product remains which, after recrystallization from toluene, melts at 226°-228° C.

Workup

  1. temperatureto cool
  2. customThe organic phase is separated off
  3. washwashed several times with a little water
  4. customuntil the reaction on pH paper
  5. customThe organic phase is dried
  6. customevaporated on a vacuum rotary evaporator
  7. customafter recrystallization from toluene, melts at 226°-228° C.

Sources & evidence

ORD record
ord-1a92da1e5a4a4bb884d248916f47715e
Source dataset
uspto-grants-1993_03
Patent number
US05192642

Reaction notes

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