Alpha-Methylstyrene → HCID 68601851, compound

HRID 1952282Notes

Reaction equation

HRID 1952282 reaction equation
[CH3:1][O:2][C:3]1[C:4](=[O:10])[CH:5]=[CH:6][C:7](=[O:9])[CH:8]=1.[CH3:11][C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[CH2:13]>C(O)(C)C>[CH3:1][O:2][C:3]1[C:4](=[O:10])[C:5]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:12]([CH3:13])=[CH:11][C:6]=2[C:7](=[O:9])[CH:8]=1

Participants

4

Reactant 2

HCID 7407Alpha-MethylstyreneHCID 761462-Methoxy-1,4-benzoquinone

Product 1

HCID 68601851HCID 68601851, compoundYield 2.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

2-Methoxy-1,4-benzoquinone (30.0 g, 72 mM) and α-Methylstyrene (236 g, 2.0 M) were dissolved in 290 ml of isopropanol and refluxed for 30 hours. The reaction solution was subjected to vacuum distillation to recover isopropanol and α-Methylstyrene, and the reaction solution was concentrated. The resulting product was purified by chromatography to give to 1.38 g (5.47 mM) of 3-Methoxy-9-methyl-1,4-phenanthrenequinone.

Workup

  1. temperaturerefluxed for 30 hours
  2. distillationThe reaction solution was subjected to vacuum distillation
  3. customto recover isopropanol and α-Methylstyrene
  4. concentrationthe reaction solution was concentrated
  5. customThe resulting product was purified by chromatography

Sources & evidence

ORD record
ord-9532de2aeae74326a4408ea5fd1819a5
Source dataset
uspto-grants-2013_03
Patent number
US08404869B2

Reaction notes

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