Hydrochloric Acid → HCID 18366008, compound

HRID 380738Notes

Reaction equation

HRID 380738 reaction equation
[CH2:1]([O:8][CH:9]1[CH2:13][O:12][CH2:11][CH:10]1[O:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][C:22]=1[O:23][CH3:24])[C:18]#N)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-:25].[K+].[OH2:27].Cl>OCC(CO)O>[CH2:1]([O:8][CH:9]1[CH2:13][O:12][CH2:11][CH:10]1[O:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][C:22]=1[O:23][CH3:24])[C:18]([OH:27])=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 18365999HCID 18365999, compound

Product 1

HCID 18366008HCID 18366008, compound

Reagents, catalysts & solvents 1

HCID 753GlycerolSolvent

Procedure

2.8 g (8.6 mmol) of 3-(4-benzyloxytetrahydrofuran-3-yloxy)-4-methoxybenzonitrile (A8) and 4.8 g (86.0 mmol) of potassium hydroxide are heated at 140° C. for 3 h in 30 ml of glycerol. The mixture is treated with 70 ml of water and acidified by dropwise addition of 40 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. For further purification, the product is chromatographed on silica gel [toluenelethyl acetate =2:1]. The product-containing fractions are concentrated and the residue is crystallized from isopropanol. 2.1 g of the title compound of m.p. 153-156° C. are obtained.

Workup

  1. temperaturecooling
  2. filtrationfiltered
  3. washthe precipitate is washed with ice water
  4. customFor further purification
  5. customthe product is chromatographed on silica gel [toluenelethyl acetate =2:1]
  6. concentrationThe product-containing fractions are concentrated
  7. customthe residue is crystallized from isopropanol

Sources & evidence

ORD record
ord-d827381de29d41138661886c6a7b08c8
Source dataset
uspto-grants-2001_10
Patent number
US06303789B1

Reaction notes

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