Boric Acid → 1-(3,5-dimethoxyphenyl)-2-(4-methoxyphenyl)ethanone

HRID 424024Notes

Reaction equation

HRID 424024 reaction equation
B(O)(O)O.[CH3:5][O:6][C:7]1[CH:8]=[C:9]([C:15](=[O:29])[CH:16]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)C(OC)=O)[CH:10]=[C:11]([O:13][CH3:14])[CH:12]=1>CC(OC)(C)C>[CH3:5][O:6][C:7]1[CH:8]=[C:9]([C:15](=[O:29])[CH2:16][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)[CH:10]=[C:11]([O:13][CH3:14])[CH:12]=1

Participants

4

Reactant 2

HCID 7628Boric AcidHCID 24788471HCID 24788471, compound

Product 1

HCID 6418291-(3,5-dimethoxyphenyl)-2-(4-methoxyphenyl)ethanoneYield 54.4%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
80 °C

Procedure

26.7 g of boric acid (0.43 mol) and 74.4 g of crude methyl 3-(3,5-dimethoxyphenyl)-2-(4-methoxyphenyl)-3-oxopropionate (0.216 mol) prepared according to Example 1 are introduced into a round-bottomed flask equipped with a distillation head. Heating is carried out, the temperature being brought gradually to 100° C. for 1 h, 120° C. for 1 h, 140° C. for 1 h and then 160° C. for 4 h while distilling off light products. The mixture is cooled to 80° C., 250 ml of water and then 200 ml of toluene are added, the mixture is kept stirred at 60° C. for 1 h, separation by settling is then carried out and the toluene phase is recovered, washed with 100 ml of a saturated aqueous sodium bicarbonate solution and concentrated on a rotary evaporator. The crude oily product obtained is taken up in 200 ml of MTBE to precipitate the product, which is filtered off and dried. Thus, after drying, 33.6 g of 1-(3,5-dimethoxyphenyl)-2-(4-methoxyphenyl)ethanone are obtained in the form of a cream-white solid, i.e. a yield of 54.4% with respect to the crude starting β-ketoester. M.p.: 93-4° C.

Workup

  1. additionare introduced into a round-bottomed flask
  2. customequipped with a distillation head
  3. temperatureHeating
  4. distillation160° C. for 4 h while distilling off light products
  5. addition250 ml of water and then 200 ml of toluene are added
  6. customseparation
  7. customthe toluene phase is recovered
  8. washwashed with 100 ml of a saturated aqueous sodium bicarbonate solution
  9. concentrationconcentrated on a rotary evaporator
  10. customThe crude oily product obtained
  11. customto precipitate the product, which
  12. filtrationis filtered off
  13. customdried
  14. customThus, after drying

Sources & evidence

ORD record
ord-958c942dc9104b4f9b8471b1f8744eb2
Source dataset
uspto-grants-2012_01
Patent number
US08101804B2

Reaction notes

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