Ethanol → HCID 20226828, compound

HRID 1732181Notes

Reaction equation

HRID 1732181 reaction equation
[Na].C(OCC)(=O)[CH2:3][C:4](C)=[O:5].[Cl:11][C:12]1[CH:13]=[C:14]([CH:20]=[CH:21][C:22]=1[C:23](=O)[C:24](=[CH2:27])[CH2:25][CH3:26])[O:15][CH2:16][C:17]([OH:19])=[O:18].[OH-].[Na+].[CH2:31](O)C>O>[Cl:11][C:12]1[CH:13]=[C:14]([CH:20]=[CH:21][C:22]=1[C:23]1[CH:24]([CH2:27][CH3:31])[CH2:25][CH2:26][C:4](=[O:5])[CH:3]=1)[O:15][CH2:16][C:17]([OH:19])=[O:18]

Participants

7

Reactant 5

HCID 702EthanolHCID 8868Ethyl AcetoacetateHCID 14798Sodium HydroxideHCID 5360545SodiumHCID 12395525HCID 12395525, compound

Product 1

HCID 20226828HCID 20226828, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of sodium (0.95 g, 0.0414 mole) in ethanol (75 ml) and ethyl acetoacetate (5.38 g, 0.0414 mole) was added [3-chloro-4-(2-methylene-1-oxobutyl)phenoxy]acetic acid (4.94 g, 0.0184 mole). The reaction mixture was heated at reflux for 3 hours. 1N sodium hydroxide (10 ml) and 55 ml of water was added and refluxing was continued for 11/2 hours, then the solvent was distilled at reduced pressure. The residue was acidified, extracted with ether, washed with water, dried over magnesium sulfate to give 4.1 g of [3-chloro-4-(6-ethyl-3-oxo-1-cyclohexen-1-yl)phenoxy]acetic acid which melted at 138°-140° C. after recrystallization from butyl chloride and methanol.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 3 hours
  3. temperaturerefluxing
  4. custom2 hours
  5. distillationthe solvent was distilled at reduced pressure
  6. extractionextracted with ether
  7. washwashed with water
  8. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-1b7d14d021284d6a96841c6cea31fe40
Source dataset
uspto-grants-1986_11
Patent number
US04625047

Reaction notes

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