Trichloroacetic Acid → 5-Isopropylazulene

HRID 1165895Notes

Reaction equation

HRID 1165895 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
  4. customto obtain the crude product (19)
  5. customThe crude product was purified on an alumina (20 g) column
  6. washeluting with hexane

Sources & evidence

ORD record
ord-b32aa31e68ba4e98b2f6fcd4dffaebe3
Source dataset
uspto-grants-1990_03
Patent number
US04912134

Reaction notes

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