Boric Acid → HCID 66674733, compound

HRID 424026Notes

Reaction equation

HRID 424026 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11](=[O:27])[CH:12]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([O:25][CH3:26])[CH:18]=2)C(OC)=O)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.B(O)(O)O>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11](=[O:27])[CH2:12][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([O:25][CH3:26])[CH:18]=2)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1

Participants

3

Reactant 2

HCID 7628Boric AcidHCID 66674198HCID 66674198, compound

Product 1

HCID 66674733HCID 66674733, compound

Conditions

Temperature
140 °C

Procedure

90.9 g of crude methyl 3-(3,5-dimethoxyphenyl)-2-(3,4-dimethoxyphenyl)-3-oxopropionate prepared according to Example 3 and 30 g of boric acid are introduced into a 250 ml three-necked round-bottomed flask. The mixture is heated with stirring at 100° C. for 1 h, 120° C. for 1 140° C. for 1 h and then 160° C. for 4 h while distilling off light products. The mixture is cooled to approximately 60° C., 226 g of a 15% sodium hydroxide solution are added dropwise and the mixture is maintained at reflux for 2 h with stirring. The reaction medium is extracted at ambient temperature with 350 ml of toluene, which is washed with 100 ml of water. The organic phase is concentrated to recover 51.70 g of 1-(3,5-dimethoxyphenyl)-2-(3,4-dimethoxyphenyl)ethanone in the form of an oil with a dark brown colour.

Workup

  1. additionare introduced into a 250 ml three-necked round-bottomed flask
  2. temperatureThe mixture is heated
  3. distillation160° C. for 4 h while distilling off light products
  4. temperatureThe mixture is cooled to approximately 60° C.
  5. addition226 g of a 15% sodium hydroxide solution are added dropwise
  6. temperaturethe mixture is maintained
  7. temperatureat reflux for 2 h
  8. stirringwith stirring
  9. extractionThe reaction medium is extracted at ambient temperature with 350 ml of toluene, which
  10. washis washed with 100 ml of water
  11. concentrationThe organic phase is concentrated
  12. customto recover 51.70 g of 1-(3,5-dimethoxyphenyl)-2-(3,4-dimethoxyphenyl)ethanone in the form of an oil with a dark brown colour

Sources & evidence

ORD record
ord-20194bd4da8d49ed85fef603c7a656dc
Source dataset
uspto-grants-2012_01
Patent number
US08101804B2

Reaction notes

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