Sodium Hydroxide → Phenol

HRID 611204Notes

Reaction equation

HRID 611204 reaction equation
Cl.[O:2]1[C:6]2[CH2:7][NH:8][CH2:9][CH2:10][C:5]=2[CH:4]=[CH:3]1.[OH-].[Na+].O1C2CNCCC=2C=C1.[C:22](=O)([O:30][CH2:31][CH2:32][CH2:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[O:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>O.N1C=CC=CC=1>[C:35]1([CH2:34][CH2:33][CH2:32][CH2:31][O:30][C:22]([N:8]2[CH2:9][CH2:10][C:5]3[CH:4]=[CH:3][O:2][C:6]=3[CH2:7]2)=[O:23])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.[C:24]1([OH:23])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 9816881Phenyl 4-phenylbutyl CarbonateHCID 154293314,5,6,7-Tetrahydrofuro[2,3-C]pyridineHCID 195999074,5,6,7-Tetrahydrofuro[2,3-c]pyridine hydrochloride

Product 2

HCID 996PhenolHCID 196002026-(4-Phenylbutoxycarbonyl)-4,5,6,7-tetrahydrofuro[2,3-c]pyridine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

4,5,6,7-Tetrahydrofuro[2,3-c]pyridine hydrochloride 0.280 g (1.754 mmol) was dissolved in water. The solution was alkalified with aqueous sodium hydroxide and extracted with dichloromethane 3 times. The combined organic layer was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. A solution of the resulting crude 4,5,6,7-tetrahydrofuro[2,3-c]pyridine and 0.71 g (2.6 mmol) of phenyl 4-phenylbutyl carbonate in 10 ml of pyridine was stirred at 100° C. overnight. The solvent was distilled off under reduced pressure; the resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=15/1 to 9/1) to yield 6-(4-phenylbutoxycarbonyl)-4,5,6,7-tetrahydrofuro[2,3-c]pyridine as a mixture with phenol.

Workup

  1. extractionextracted with dichloromethane 3 times
  2. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=15/1 to 9/1)

Sources & evidence

ORD record
ord-359843f0692a49a182fc3bbf482bea6d
Source dataset
uspto-grants-1999_12
Patent number
US05998433

Reaction notes

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