Ethyl 2-methylacetoacetate → HCID 13749104, compound

HRID 1732173Notes

Reaction equation

HRID 1732173 reaction equation
C[O-:2].[Na+].Cl.[Cl:5][C:6]1[C:16]([Cl:17])=[C:15]([C:18](=O)[CH2:19][CH2:20]N(C)C)[CH:14]=[CH:13][C:7]=1[O:8][CH2:9][C:10]([OH:12])=[O:11].C(O[C:28](=O)[CH:29](C)[C:30]([CH3:32])=O)C>C(O)C>[Cl:5][C:6]1[C:16]([Cl:17])=[C:15]([C:18]2[CH2:32][CH2:30][CH:29]([CH3:28])[C:20](=[O:2])[CH:19]=2)[CH:14]=[CH:13][C:7]=1[O:8][CH2:9][C:10]([OH:12])=[O:11]

Participants

5

Reactant 3

HCID 701Ethyl 2-methylacetoacetateHCID 10942334Sodium MethoxideHCID 70419362HCID 70419362, compound

Product 1

HCID 13749104HCID 13749104, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of sodium methoxide (3.5 g, 0.065 mole) in ethanol (100 ml) and ethyl-2-methylacetoacetate (6.6 ml) was added [2,3-dichloro-4-(3-dimethylamino-1-oxopropyl)phenoxy]acetic acid hydrochloride (7.4 g, 0.021 mole). The reaction mixture was heated at reflux for 3 hours then the solvent was distilled at reduced pressure, treated with 100 ml of 2% sodium hydroxide, heated on a steam bath for 11/2 hours, then acidified, extracted with ether, washed with water, dried over magnesium sulfate and evaporated at reduced pressure. The residue was triturated with 100 ml of hot toluene, filtered, and dried to give 0.9 of [2,3-dichloro-4-(4-methyl-3-oxo-1-cyclohexen-1-yl)phenoxy]acetic acid which melted at 183°-185° C. after recrystallization from 30 ml of toluene.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 3 hours
  3. distillationthe solvent was distilled at reduced pressure
  4. additiontreated with 100 ml of 2% sodium hydroxide
  5. temperatureheated on a steam bath for 11/2 hours
  6. extractionextracted with ether
  7. washwashed with water
  8. dry with materialdried over magnesium sulfate
  9. customevaporated at reduced pressure
  10. customThe residue was triturated with 100 ml of hot toluene
  11. filtrationfiltered
  12. customdried

Sources & evidence

ORD record
ord-6580a3fa9f994460bf225831939458ae
Source dataset
uspto-grants-1986_11
Patent number
US04625047

Reaction notes

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