Trichloroacetic Acid → 5-Isopropylazulene

HRID 1723190Notes

Reaction equation

HRID 1723190 reaction equation
C([C:4]1[C:13]2[C:7]([CH:8]=[CH:9][CH:10]=[C:11]([CH:14]([CH3:16])[CH3:15])[CH:12]=2)=[CH:6][CH:5]=1)(O)=O.ClC(Cl)(Cl)C(O)=O>C1C=CC=CC=1>[CH:14]([C:11]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:13](=[CH:4][CH:5]=[CH:6]2)[CH:12]=1)([CH3:16])[CH3:15]

Participants

4

Reactant 2

HCID 6421Trichloroacetic AcidHCID 145157441-Carboxy-7-isopropylazulene

Product 1

HCID 156026265-Isopropylazulene

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The well-dried compound (18) (2.1 g) was dissolved in benzene (150 ml), and then trichloroacetic acid (0.4 g) was added. The mixture was heated under reflux for 2 hours on an oil bath. The reaction mixture was cooled to room temperature, and then passed through a column of alumina. From the eluted solution the solvent was distilled off to obtain the crude product (19), at a yield of 1.02 g. The crude product was purified on an alumina (20 g) column, eluting with hexane, to obtain the product (19) at a yield of 725 mg (91.2%) as a blue oily substance.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2 hours on an oil bath
  3. distillationFrom the eluted solution the solvent was distilled off

Sources & evidence

ORD record
ord-01e603285fe0488093a5bf3ceb0db887
Source dataset
uspto-grants-1989_08
Patent number
US04859701

Reaction notes

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