Sulfuric Acid → 2-Benzyltoluene

HRID 1764609Notes

Reaction equation

HRID 1764609 reaction equation
B(F)(F)F.P(=O)(O)(O)O.S(=O)(=O)(O)O.[CH3:15][C:16]1[C:21]([CH2:22]Cl)=[CH:20][CH:19]=[CH:18][CH:17]=1>C1C=CC=CC=1>[CH2:22]([C:21]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH3:15])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 11093alpha-Chloro-o-xyleneHCID 11480637Phosphoric acid;trifluoroborane

Product 1

HCID 697382-BenzyltolueneYield 91.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

470 parts of benzene are emulsified in a mixture of 200 parts of boron fluoride-phosphoric acid (containing 90 parts of boron fluoride in 110 parts of phosphoric acid) and 200 parts of sulfuric acid (85% strength by weight) by stirring thoroughly. A solution of 140 parts of o-xylyl chloride in 470 parts of benzene is added at from 75° to 80° C in the course of 2 hours. The reaction mixture is stirred for a further 5 hours at from 75° to 80° C and the organic phase is then separated off. 167 parts (91.8% of theory) of o-benzyltoluene (nD25 : 1.5739) are isolated by fractional distillation at from 98° to 100° C at 0.2 mm Hg.

Workup

  1. stirringThe reaction mixture is stirred for a further 5 hours at from 75° to 80° C
  2. customthe organic phase is then separated off

Sources & evidence

ORD record
ord-bf4d8efdb36b46f2911ed5caa699121d
Source dataset
uspto-grants-1978_09
Patent number
US04117019

Reaction notes

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