Potassium Carbonate → HCID 131716351, compound

HRID 1165981Notes

Reaction equation

HRID 1165981 reaction equation
[CH2:1]([O:5][C:6](=[O:16])[CH:7]=[CH:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH3:4].C(=O)([O-])[O-].[K+].[K+].[C:23](Br)#[C:24][CH2:25]C>CC(C)=O>[CH2:1]([O:5][C:6](=[O:16])[CH:7]=[CH:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:25][C:24]#[CH:23])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 109970821-Bromobut-1-yneHCID 54465584Butyl 3-(4-hydroxyphenyl)prop-2-enoate

Product 1

HCID 131716351HCID 131716351, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
56 °C

Procedure

903 g (4.1M) of p-hydroxy cinnamic acid n-butyl ester (see above) are dissolved in 4 liter acetone. 622 g (4.5M) of finely powdered potassium carbonate and 523.5 g (4.4M) freshly distilled butinyl bromide are added. Under stirring the suspension is heated to reflux (temperature in the mixture 56° C.). After refluxing for about 18 hours the starting material is consumed. The yellow suspension is cooled to about 10° C. and filtered. The filtrate is evaporated to dryness in vacuo (about 12 mbar) at 35° C. The yellow oily residue is added with stirring to about 6 liters of water. A white crystalline precipitate is obtained which is isolated by filtration. The solid material is washed with water and dried. It is crystallised from 1 liter of hexane. The product, 805.5 g, is obtained in colourless prisms, mp 38.5° to 39.0° C. From the mother liquor another 183.0 g of product could be isolated. Total yield 988.5 g (93.3% of theory).

Workup

  1. temperatureis heated
  2. temperatureAfter refluxing for about 18 hours the starting material
  3. customis consumed
  4. temperatureThe yellow suspension is cooled to about 10° C.
  5. filtrationfiltered
  6. customThe filtrate is evaporated to dryness in vacuo (about 12 mbar) at 35° C
  7. additionThe yellow oily residue is added
  8. stirringwith stirring to about 6 liters of water
  9. customA white crystalline precipitate is obtained which
  10. customis isolated by filtration
  11. washThe solid material is washed with water
  12. customdried
  13. customIt is crystallised from 1 liter of hexane
  14. customThe product, 805.5 g, is obtained in colourless prisms, mp 38.5° to 39.0° C

Sources & evidence

ORD record
ord-05ff3c42d22d4dd5b9da8ba484c87c4c
Source dataset
uspto-grants-1990_03
Patent number
US04912241

Reaction notes

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