Benzyl Alcohol → HCID 19795269, compound

HRID 1886129Notes

Reaction equation

HRID 1886129 reaction equation
[CH2:1]([S:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:15](O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[H+].[B-:24]([F:28])([F:27])([F:26])[F:25]>C(Cl)Cl.C(OCC)C>[F:25][B-:24]([F:28])([F:27])[F:26].[CH2:1]([S+:8]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 244Benzyl AlcoholHCID 13255Benzyl phenyl sulphideHCID 28118Tetrafluoroboric acid

Product 1

HCID 19795269HCID 19795269, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 75.0 g (0.374 mol) of benzylphenyl sulfide, 60.73 g (0.561 mol) of benzyl alcohol in 350 ml of methylene chloride is introduced into a reaction vessel provided with a stirrer and thermometer. 182.45 g (1.12 mol) of 54% by weight HBF4 in diethyl ether are added dropwise at an internal temperature of 20°-30° C. in the course of 35 min, while stirring. The reaction mixture is then stirred at RT for 2 h. The reaction mixture is diluted with 300-400 ml of methylene chloride and extracted 4 times with water (pH ~6). The organic phase is then dried over MgSO4 and the solvent is removed on a rotary evaporator. The yellow-brown oil which remains is stirred in 400 ml of toluene and the mixture is left to crystallize at 0°-5° C. for about 1 h. The suspension is filtered and the residue is washed with a little cooled toluene (0°-5° C.). The pure product is dried under a high vacuum at RT overnight. 123.8 g (87% of theory) of dibenzylphenylsulfonium tetrafluoroborate are obtained as white crystals of melting point 110°-115° C.

Workup

  1. customprovided with a stirrer
  2. stirringThe reaction mixture is then stirred at RT for 2 h
  3. extractionextracted 4 times with water (pH ~6)
  4. dry with materialThe organic phase is then dried over MgSO4
  5. customthe solvent is removed on a rotary evaporator
  6. stirringThe yellow-brown oil which remains is stirred in 400 ml of toluene
  7. waitthe mixture is left
  8. customto crystallize at 0°-5° C. for about 1 h
  9. filtrationThe suspension is filtered
  10. washthe residue is washed with
  11. temperaturea little cooled toluene (0°-5° C.)
  12. customThe pure product is dried under a high vacuum at RT overnight

Sources & evidence

ORD record
ord-ec2c8cb852674ab493f83b1e4a688a9d
Source dataset
uspto-grants-1992_09
Patent number
US05149767

Reaction notes

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