Methanol → HCID 13796792, compound

HRID 567622Notes

Reaction equation

HRID 567622 reaction equation
C[OH:2].[OH-].[K+].[OH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]#[N:19])=[CH:14][CH:13]=2)=[CH:8][CH:7]=1.O.[CH3:21][CH2:22][CH2:23]CCC>ClCCl>[OH:2][CH2:23][CH2:22][CH2:21][O:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]#[N:19])=[CH:14][CH:13]=2)=[CH:10][CH:11]=1

Participants

7

Reactant 5

HCID 887MethanolHCID 962WaterHCID 8058HexaneHCID 14797Potassium HydroxideHCID 1406104'-Hydroxy-4-biphenylcarbonitrile

Product 1

HCID 13796792HCID 13796792, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 400 ml of a methanol solution having 5.7 wt % potassium hydroxide, 50 g of the compound 6 and 49.1 g of 4-hydroxy-4′-cyanobiphenyl were added, followed by reflux. After they were completely reacted, water and dichloromethane were added thereto, and the organic layer was extracted. Then, saturated aqueous sodium chloride was added thereto, and the organic layer was extracted, followed by washing with water. Anhydrous magnesium sulfate was added thereto, the mixture was subjected to filtration under reduced pressure, and the filtrate was extracted. The filtrate was subjected to column chromatography by using dichloromethane as a developing solution, and dichloromethane was distilled off at 30° C. to obtain powder crystals. n-Hexane was added thereto to conduct recrystallization, and 40.0 g of the compound 7, i.e. 4-(3-hydroxypropyloxy)-4′-cyanobiphenyl was obtained.

Workup

  1. additionwere added
  2. temperatureby reflux
  3. customAfter they were completely reacted
  4. extractionthe organic layer was extracted
  5. additionThen, saturated aqueous sodium chloride was added
  6. extractionthe organic layer was extracted
  7. washby washing with water
  8. additionAnhydrous magnesium sulfate was added
  9. filtrationthe mixture was subjected to filtration under reduced pressure
  10. extractionthe filtrate was extracted
  11. distillationwas distilled off at 30° C.
  12. customto obtain powder crystals
  13. customrecrystallization, and 40.0 g of the compound 7

Sources & evidence

ORD record
ord-b5c5f424c13447aa852128a4542ea385
Source dataset
uspto-grants-2001_01
Patent number
US06180028B2

Reaction notes

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