Methanol → HCID 18424529, compound

HRID 1282408Notes

Reaction equation

HRID 1282408 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=O)=[C:4]([CH:12]=[CH:13][C:14](OC)=O)[CH:3]=1.[CH3:18][O-:19].[Na+].C[OH:22]>>[C:18]([CH2:14][CH:13]1[CH2:12][C:4]2[C:5](=[CH:10][CH:11]=[C:2]([Cl:1])[CH:3]=2)[C:6]1=[O:8])([OH:22])=[O:19]

Participants

4

Reactant 3

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 69978143Methyl 4-Chloro-2-(3-methoxy-3-oxo-1-propenyl)-benzoate

Product 1

HCID 18424529HCID 18424529, compound

Conditions

Temperature
70 °C

Procedure

108 g of methyl 4-chloro-2-(3-methoxy-3-oxo-1-propenyl)-benzoate are dissolved in 300 ml of methanol, and 80 g of sodium methoxide are then added. The mixture is then heated at 70° C. and some of the methanol is distilled off, such that the reaction mixture can still be stirred. After 2 h, 400 ml of toluene are added slowly, and the remaining methanol is removed. The mixture is then stirred for another 0.5 h and then cooled to room temperature. 10 g of acetic acid are then added dropwise to the mixture, which is then diluted with 500 ml of water and adjusted to pH 4-5 using 1 N hydrochloric acid. The toluene phase is concentrated until the product precipitates. Following filtration, the product can be recrystallized from hexane. This gives 93.5 g of 2-carboxymethyl-5-chloroindan-1-one.

Workup

  1. distillationsome of the methanol is distilled off, such that the reaction mixture
  2. addition400 ml of toluene are added slowly
  3. customthe remaining methanol is removed
  4. stirringThe mixture is then stirred for another 0.5 h
  5. temperaturecooled to room temperature
  6. addition10 g of acetic acid are then added dropwise to the mixture, which
  7. additionis then diluted with 500 ml of water
  8. concentrationThe toluene phase is concentrated until the product
  9. customprecipitates
  10. filtrationfiltration
  11. customthe product can be recrystallized from hexane

Sources & evidence

ORD record
ord-9659fb099e7d4de480978efd1900a706
Source dataset
uspto-grants-2002_09
Patent number
US06455725B1

Reaction notes

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