Isopropanol → HCID 20390857, compound

HRID 426439Notes

Reaction equation

HRID 426439 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][CH2:7][C:8]2[CH:19]=[CH:18][C:11]([O:12][CH:13]([CH3:17])[C:14]([OH:16])=[O:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH:34](O)([CH3:36])[CH3:35]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][C:8]2[CH:19]=[CH:18][C:11]([O:12][CH:13]([CH3:17])[C:14]([O:16][CH:34]([CH3:36])[CH3:35])=[O:15])=[CH:10][CH:9]=2)=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 682631,1'-CarbonyldiimidazoleHCID 5259868HCID 5259868, compound

Product 1

HCID 20390857HCID 20390857, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6.1 gm of 2-[4-(4-chlorophenoxy-methyl)-phenoxy]-propionic acid was dissolved in 50 ml of absolute tetrahydrofuran, and 3.2 gm of 1,1'-carbonyldiimidazole were added to the solution. The resulting mixture was heated for a short time and was then allowed to stand at room temperature for 4 hours. Thereafter, the reaction mixture was admixed with 2.4 gm of isopropanol, and the mixture was refluxed for one hour, evaporated in vacuo in a rotary evaporator, and the oily residue was recrystallized from ethanol/water, yielding 4.5 gm (65% of theory) of the ester named in the heading, which had a melting point of 81° C.

Workup

  1. temperatureThe resulting mixture was heated for a short time
  2. temperaturethe mixture was refluxed for one hour
  3. customevaporated in vacuo in a rotary evaporator
  4. customthe oily residue was recrystallized from ethanol/water

Sources & evidence

ORD record
ord-752cf165d23c40978064c28b353da748
Source dataset
uspto-grants-1979_10
Patent number
US04169720

Reaction notes

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