2,3-Diphenylbutane-2,3-diol → 2,3-Diphenyl-1,3-butadiene

HRID 1449301Notes

Reaction equation

HRID 1449301 reaction equation
[C:1]1([C:7](O)([C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)(O)[CH3:10])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.OS([O-])(=O)=O.[K+]>>[C:1]1([C:7]([C:9]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[CH2:10])=[CH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 978862,3-Diphenylbutane-2,3-diolHCID 516920Potassium bisulfate

Product 1

HCID 41291332,3-Diphenyl-1,3-butadiene

Procedure

A mixture of 50 parts of 2,3-diphenyl-2,3-dihydroxybutane and 0.5 part of freshly dehydrated KHSO4 is distilled for 50 minutes at 11 Torr and 200° C. bath temperature. The fraction which is collected within the boiling range of 150°-180° C./11 Torr yields 43.8 parts of crude 2,3-diphenyl-1,3-butadiene. The product is stirred direct with 21.5 parts of acrylic acid and 2 parts of hydroquinone under a nitrogen atmosphere for 3 hours at 130° to 140° C.

Workup

  1. distillationis distilled for 50 minutes at 11 Torr and 200° C. bath temperature
  2. customThe fraction which is collected within the boiling range of 150°-180° C./11 Torr

Sources & evidence

ORD record
ord-6523644be13140489bf1ec30bf280485
Source dataset
uspto-grants-1980_02
Patent number
US04190433

Reaction notes

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