Ethanol → HCID 13749108, compound

HRID 1732176Notes

Reaction equation

HRID 1732176 reaction equation
[Na].C(OCC)(=O)[CH2:3][C:4](C)=[O:5].[Cl:11][C:12]1[C:22]([Cl:23])=[C:21]([C:24](=O)[CH:25]=[C:26]([CH3:28])[CH3:27])[CH:20]=[CH:19][C:13]=1[O:14][CH2:15][C:16]([OH:18])=[O:17].[CH2:30](O)C>>[Cl:11][C:12]1[C:22]([Cl:23])=[C:21]([C:24]2[CH2:25][C:26]([CH3:28])([CH3:30])[CH2:27][C:4](=[O:5])[CH:3]=2)[CH:20]=[CH:19][C:13]=1[O:14][CH2:15][C:16]([OH:18])=[O:17]

Participants

5

Reactant 4

HCID 702EthanolHCID 8868Ethyl AcetoacetateHCID 5360545SodiumHCID 70453603HCID 70453603, compound

Product 1

HCID 13749108HCID 13749108, compound

Procedure

To a stirred solution of sodium (1.449 g, 0.063 mole) in ethanol (150 ml) and ethyl acetoacetate (8.20 g, 0.063 mole) was added (2,3-dichloro-4-(3-methyl-1-oxo-2-butenyl)phenoxy]acetic acid (9.09 g, 0.03 mole). The reaction mixture was heated at reflux for 31/2 hours then the solvent was distilled at reduced pressure. The residue was acidified with hydrochloric acid, extracted with ether and sodium bicarbonate, acidified with hydrochloric acid, extracted with ether and methylene chloride, washed with water, dried over magnesium sulfate, and evaporated at reduced pressure to give 4.5 g of [2,3-dichloro-4-(5,5-dimethyl-3-oxo-1-cyclohexen-1-yl)phenoxy]acetic acid which melted at 178°-180° C. after purification by chromatography on silica and recrystallization from 42 ml of acetonitrile.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 31/2 hours
  3. distillationthe solvent was distilled at reduced pressure
  4. extractionextracted with ether and sodium bicarbonate
  5. extractionextracted with ether and methylene chloride
  6. washwashed with water
  7. dry with materialdried over magnesium sulfate
  8. customevaporated at reduced pressure

Sources & evidence

ORD record
ord-98750c20519e44fcb79d78bc5153e801
Source dataset
uspto-grants-1986_11
Patent number
US04625047

Reaction notes

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