Phosphoric Acid → HCID 10244283, compound

HRID 413503Notes

Reaction equation

HRID 413503 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8](O)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.P(=O)(O)(O)O>O>[C:10]1(/[CH:9]=[CH:8]/[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Br:1])[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 1004Phosphoric AcidHCID 12715432HCID 12715432, compound

Product 1

HCID 10244283HCID 10244283, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
170 °C

Procedure

A stirred mixture of 1-(2-bromophenyl)-2-phenylethan-1-ol (15.50 g) and orthophosphoric acid (150 ml) was heated at 170° C. for 1 hour and then poured into iced water and extracted with ether. The extracts were washed with water, dried and concentrated to give the crude product as an orange oil (14.29 g). Evaporative distillation (0.3 torr; oven temperature 140° C.) gave E-1-phenyl-2(2-bromophenyl)ethylene (12.53 g, 86% yield) as a pale yellow oil with a purity of 97% by GC.

Workup

  1. extractionextracted with ether
  2. washThe extracts were washed with water
  3. customdried
  4. concentrationconcentrated
  5. customto give the crude product as an orange oil (14.29 g)
  6. distillationEvaporative distillation (0.3 torr; oven temperature 140° C.)

Sources & evidence

ORD record
ord-0b867b56e1cd49ae8b0022a1c1baab6c
Source dataset
uspto-grants-2003_05
Patent number
US06566547B1

Reaction notes

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