Ethanol → HCID 14515739, compound

HRID 1165891Notes

Reaction equation

HRID 1165891 reaction equation
[C:1]([C:4]1[C:13]2[C:7]([CH:8]=[CH:9][C:10]([CH:14]([CH3:16])[CH3:15])=[CH:11][CH:12]=2)=[C:6]([CH2:17][CH3:18])[CH:5]=1)([OH:3])=[O:2].[C:19](Cl)(=O)[C:20](Cl)=O.C(O)C>C1C=CC=CC=1>[CH2:19]([O:2][C:1]([C:4]1[C:13]2[C:7]([CH:8]=[CH:9][C:10]([CH:14]([CH3:15])[CH3:16])=[CH:11][CH:12]=2)=[C:6]([CH2:17][CH3:18])[CH:5]=1)=[O:3])[CH3:20]

Participants

5

Reactant 3

HCID 702EthanolHCID 65578Oxalyl chlorideHCID 14515738HCID 14515738, compound

Product 1

HCID 14515739HCID 14515739, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The above-mentioned azulene carboxylic acid (3) (4.84 g, 0.002 mole) is suspended in benzene (100 ml), and oxalyl chloride (2.8 g, 0.02 mole) is added dropwise thereto under cooling with ice. The mixture is stirred for 3 hours at room temperature and cooled with ice again. Ethyl alcohol (100 ml) is added dropwise thereto and stirred for 2 hours at room temperature. The mixture is poured into ice-water (300 ml) and extracted with benzene (100 ml). The benzene layer is separated, and then washed with water. The benzene solution is concentrated under reduced pressure, and n-hexane is added thereto to obtain the ethyl ester derivative (2) at a yield of 4.5 g, 83.3%, having a melting point of 48° to 49° C.

Workup

  1. temperatureunder cooling with ice
  2. temperaturecooled with ice again
  3. stirringstirred for 2 hours at room temperature
  4. extractionextracted with benzene (100 ml)
  5. customThe benzene layer is separated
  6. washwashed with water
  7. concentrationThe benzene solution is concentrated under reduced pressure, and n-hexane
  8. additionis added

Sources & evidence

ORD record
ord-e525f213064745cfb70100565a8d97cc
Source dataset
uspto-grants-1990_03
Patent number
US04912134

Reaction notes

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