Water → Dibenzyl

HRID 1589579Notes

Reaction equation

HRID 1589579 reaction equation
[C:1]1([CH3:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O>ClCCl>[C:1]1(/[CH:7]=[CH:7]/[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:1]1([CH2:7][CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 962WaterHCID 1140Toluene2×

Product 2

HCID 7647DibenzylYield 35%HCID 638088trans-StilbeneYield 15%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

In this example the substrate was toluene. Helium was fed into the bottom chamber of the reactor at 3.6 mL/min, and toluene and water were added to the carrier gas at a rate of 1.0 mmol/h and 2.0 mmol/h, respectively, by syringe pump. Air was passed through the top chamber of the reactor at the rate of 3.6 mL per min. The reaction was run at 600° C., and a scrubber containing 5.0 mL of dichloromethane cooled to 0° C. was used to collect the reaction products. Nonane and tetradecane were used as g.c. internal standards. At 2.0% conversion, a 50% selectivity to toluene dimers (15% trans-stilbene and 35% bibenzyl) was obtained.

Workup

  1. additionwere added to the carrier gas at a rate of 1.0 mmol/h and 2.0 mmol/h
  2. customwas run at 600° C.
  3. customto collect the reaction products

Sources & evidence

ORD record
ord-f3556c8a32f545f3b6f7819f7e638006
Source dataset
uspto-grants-1986_02
Patent number
US04571443

Reaction notes

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