Crotyl chloride → HCID 67550030, compound

HRID 2214318Notes

Reaction equation

HRID 2214318 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([OH:16])=[O:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[OH-].[K+].[CH2:19](Cl)[CH:20]=[CH:21][CH3:22]>C(O)C>[CH2:19]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([OH:16])=[O:15])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1)[CH:20]=[CH:21][CH3:22]

Participants

5

Reactant 3

HCID 11589Crotyl chlorideHCID 14797Potassium HydroxideHCID 3015564'-Hydroxy-4-biphenylcarboxylic acid

Product 1

HCID 67550030HCID 67550030, compoundYield 49.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

8.6 g of 4′-hydroxy-4-biphenylcarboxylic acid was added to hydrous ethanol containing 5.3 g of potassium hydroxide dissolved therein, followed by stirring at room temperature for 30 minutes. While heating at reflux, 5.5 g of crotyl chloride was added dropwise, followed by heating at reflux for 2 hours. After the completion of the reaction, ethanol was distilled off under reduced pressure and 50 ml of 18% HCl was added to deposit a crystal. The deposited crystal was collected by filtration, washed with water and then dried under reduced pressure to obtain 5.3 g of 4′-(2-butenyloxy)-4-biphenylcarboxylic acid (XI-k). Excess thionyl chloride was added, followed by heating at reflux for 2 hours. After the completion of the reaction, excess thionyl chloride was distilled off under reduced pressure. Then, 30 ml of pyrimidine and 2.6 g of (R)-1-(3-methoxyphenyl)ethanol (XI-l) were added to the resulting crude product and the reaction was conducted at 50° C. for one hour. After the completion of the reaction, the reaction product was extracted with toluene in the presence of hydrochloric acid, washed with water and dried, and then the solvent was distilled off under reduced pressure. The residue was recrystallized from methanol to obtain 5.1 g of 1-(3-methoxyphenyl)ethyl (R)-4′-(2-butenyloxy)-4-biphenylcarboxylate (R-isomer of the compound represented by the formula (XI-m).

Workup

  1. dissolutiondissolved
  2. temperatureWhile heating
  3. temperatureat reflux
  4. temperatureby heating
  5. temperatureat reflux for 2 hours
  6. distillationwas distilled off under reduced pressure and 50 ml of 18% HCl
  7. additionwas added
  8. filtrationThe deposited crystal was collected by filtration
  9. washwashed with water
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-ebd915233b0543ff8b560b9f6835ee3a
Source dataset
uspto-grants-2006_09
Patent number
US07108896B2

Reaction notes

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