Potassium Carbonate → HCID 131716351, compound

HRID 1461861Notes

Reaction equation

HRID 1461861 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-f6872e215ceb4a22b45cadac37c5dd35
Source dataset
uspto-grants-1991_12
Patent number
US05077422

Reaction notes

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