Methanol → HCID 22915493, compound

HRID 2174357Notes

Reaction equation

HRID 2174357 reaction equation
C([O:3][C:4](=[O:23])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)C.[OH-].[Na+].CO>C1COCC1.O>[C:21]([C:18]1[CH:17]=[CH:16][C:15]([C:12]2[CH:13]=[CH:14][C:9]([O:8][CH2:7][CH2:6][CH2:5][C:4]([OH:23])=[O:3])=[CH:10][CH:11]=2)=[CH:20][CH:19]=1)#[N:22]

Participants

6

Reactant 3

HCID 887MethanolHCID 14798Sodium Hydroxide2×HCID 54147598HCID 54147598, compound

Product 1

HCID 22915493HCID 22915493, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(4′-cyanobiphenyl-4-yloxy)butyric acid ethyl ester (3.78 g, 12.7 mmol) in THF (50 ml) was added a solution of NaOH (1.0 g, 25 mmol) in water (1.5 ml). The mixture was stirred at room temperature for 1.5 h and then at 67° C. for 3 h. More NaOH (1 g) in water (1 ml) was added, and stirring at room temperature was continued for 15 h. MeOH (10 ml) was added, and after stirring at room temperature for 1.5 h the mixture was diluted with water (150 ml) and acidified with concentrated, aqueous HCl (6.6 ml). The product was isolated by filtration and washed with water (approx 20 ml). The solid was suspended in MeCN (50 ml), heated to reflux (no dissolution) and allowed to cool to room temperature. Filtration and drying under reduced pressure yielded 2.70 g (76%) of 4-(4′-cyanobiphenyl-4-yloxy)butyric acid as a colorless solid.

Workup

  1. waitat 67° C. for 3 h
  2. stirringstirring at room temperature
  3. waitwas continued for 15 h
  4. stirringafter stirring at room temperature for 1.5 h the mixture
  5. concentrationwith concentrated
  6. customThe product was isolated by filtration
  7. washwashed with water (approx 20 ml)
  8. temperatureheated
  9. temperatureto reflux (
  10. dissolutionno dissolution) and
  11. temperatureto cool to room temperature
  12. filtrationFiltration
  13. customdrying under reduced pressure

Sources & evidence

ORD record
ord-3ed61a33b7914c319563d8b9a3a3daf6
Source dataset
uspto-grants-2015_06
Patent number
US09061067B2

Reaction notes

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