Water → HCID 18366003, compound

HRID 380737Notes

Reaction equation

HRID 380737 reaction equation
[CH2:1]([O:3][CH:4]1[CH2:8][O:7][CH2:6][CH:5]1[O:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=1[O:18][CH3:19])[C:13]#N)[CH3:2].[OH-:20].[K+].[OH2:22]>OCC(CO)O>[CH2:1]([O:3][CH:4]1[CH2:8][O:7][CH2:6][CH:5]1[O:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=1[O:18][CH3:19])[C:13]([OH:22])=[O:20])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 18366004HCID 18366004, compound

Product 1

HCID 18366003HCID 18366003, compound

Reagents, catalysts & solvents 1

HCID 753GlycerolSolvent

Procedure

1.46 g (5.5 mmol) of 3-(4-ethoxytetrahydrofuran-3-yloxy)-4-methoxybenzonitrile (A7) and 3.0 g (55.0 mmol) of potassium hydroxide are heated at 140° C. for 3 h in 15 ml of glycerol. The mixture is treated with 50 ml of water, washed with 2×25 ml of ethyl acetate and the aqueous phase is acidified by dropwise addition of 30 ml of 2 N hydrochloric acid with ice-cooling. The mixture is subsequently stirred for 1 h, filtered and the precipitate is washed with ice water. 1.49 g of the title compound of m.p. 135-138° C. are obtained.

Workup

  1. washwashed with 2×25 ml of ethyl acetate
  2. additionthe aqueous phase is acidified by dropwise addition of 30 ml of 2 N hydrochloric acid with ice-
  3. temperaturecooling
  4. filtrationfiltered
  5. washthe precipitate is washed with ice water

Sources & evidence

ORD record
ord-603afc8bed8e4ad8a3d4d2771d823990
Source dataset
uspto-grants-2001_10
Patent number
US06303789B1

Reaction notes

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