Potassium Hydroxide → 1-Carboxy-7-isopropylazulene

HRID 1723189Notes

Reaction equation

HRID 1723189 reaction equation
[OH-].[K+].C[O:4][C:5]([C:7]1[C:16]2[C:10]([CH:11]=[CH:12][CH:13]=[C:14]([CH:17]([CH3:19])[CH3:18])[CH:15]=2)=[CH:9][CH:8]=1)=[O:6]>C(O)C.O>[C:5]([C:7]1[C:16]2[C:10]([CH:11]=[CH:12][CH:13]=[C:14]([CH:17]([CH3:19])[CH3:18])[CH:15]=2)=[CH:9][CH:8]=1)([OH:6])=[O:4]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 111388961-Methoxycarbonyl-7-isopropylazulene

Product 1

HCID 145157441-Carboxy-7-isopropylazulene

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

Potassium hydroxide (10.5 g) was dissolved in a mixture of ethanol (80 ml) and water (15 ml). The compound (17) (12.43 g) was added thereto and the mixture was heated under reflux for 50 minutes in an oil bath. The reaction solution was cooled to room temperature, and then poured into water (400 ml). The solution was made acidic (pH 3) with conc. HC1. The precipitate was filtered, washed with water and dried to obtain 1-carboxy-7-isopropylazulene (18), at a yield of 2.1 g (92.3%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 50 minutes in an oil bath
  3. filtrationThe precipitate was filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-c13a387793984a1f95d190ed9c0ab634
Source dataset
uspto-grants-1989_08
Patent number
US04859701

Reaction notes

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