4-Methylbenzyl alcohol → Tris(p-methylbenzyl)sulfonium tetrafluoroborate

HRID 1886127Notes

Reaction equation

HRID 1886127 reaction equation
[CH3:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][S:7][CH2:8][C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[CH3:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23]O)=[CH:21][CH:20]=1.[H+].[B-:28]([F:32])([F:31])([F:30])[F:29]>C(OCC)C.C(Cl)Cl>[F:29][B-:28]([F:32])([F:31])[F:30].[CH3:15][C:12]1[CH:11]=[CH:10][C:9]([CH2:8][S+:7]([CH2:18][C:19]2[CH:26]=[CH:25][C:22]([CH3:23])=[CH:21][CH:20]=2)[CH2:6][C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:17][CH:16]=2)=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 115054-Methylbenzyl alcoholHCID 28118Tetrafluoroboric acidHCID 139416Sulfide, bis(4-methylbenzyl)-

Product 1

HCID 19795292Tris(p-methylbenzyl)sulfonium tetrafluoroborate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

85.1 g (0.351 mol) of di-(p-methylbenzyl) sulfide and 51.5 g (0.421 mol) of p-methylbenzyl alcohol are initially introduced into 250 ml of methylene chloride under an N2 atmosphere in a reaction vessel (750 ml) provided with a stirrer and thermometer. 142.7 g of an approximately 54% by weight HBF4 solution in diethyl ether is added dropwise at an internal temperature of 20°-30° C. in the course of 40 min, while stirring. The reaction mixture is stirred at RT for 2 h. The reaction mixture is diluted with methylene chloride and extracted 4 times by shaking with deionized water (pH 5-6). The organic phase is dried with MgSO4 and the methylene chloride is removed on a rotary evaporator. The product, which has not been completely freed from methylene chloride, is stirred in 250 ml of toluene at RT for about 1 h and then at 0°-5° C. for 1 h. The crystals which have now precipitated are filtered off with suction and washed with a little toluene. The product is dried under a high vacuum at room temperature for 19 h. 118.6 g of tris-(p-methylbenzyl)-sulfonium tetrafluoroborate are obtained as white crystals of melting point 168°-170° C.

Workup

  1. customprovided with a stirrer
  2. stirringThe reaction mixture is stirred at RT for 2 h
  3. extractionextracted 4 times
  4. stirringby shaking with deionized water (pH 5-6)
  5. dry with materialThe organic phase is dried with MgSO4
  6. customthe methylene chloride is removed on a rotary evaporator
  7. stirringis stirred in 250 ml of toluene at RT for about 1 h
  8. customThe crystals which have now precipitated
  9. filtrationare filtered off with suction
  10. washwashed with a little toluene
  11. customThe product is dried under a high vacuum at room temperature for 19 h

Sources & evidence

ORD record
ord-be316895c7b0426c999fe579fae2b6a3
Source dataset
uspto-grants-1992_09
Patent number
US05149767

Reaction notes

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