Sodium Hydroxide → Phenol

HRID 611201Notes

Reaction equation

HRID 611201 reaction equation
Cl.[O:2]1[C:10]2[CH2:9][CH2:8][NH:7][CH2:6][C:5]=2[CH:4]=[CH:3]1.[C:11](=O)([O:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[OH-].[Na+]>N1C=CC=CC=1>[C:24]1([CH2:23][CH2:22][CH2:21][CH2:20][O:19][C:11]([N:7]2[CH2:8][CH2:9][C:10]3[O:2][CH:3]=[CH:4][C:5]=3[CH2:6]2)=[O:12])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[C:13]1([OH:12])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 9816881Phenyl 4-phenylbutyl CarbonateHCID 195999414,5,6,7-Tetrahydrofuro[3,2-c]pyridine hydrochloride

Product 2

HCID 996PhenolHCID 196000735-(4-Phenylbutoxycarbonyl)-4,5,6,7-tetrahydrofuro[3,2-c]pyridine

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 0.220 g (1.378 mmol) of 4,5,6,7-tetrahydrofuro[3,2-c]pyridine hydrochloride and 0.56 g (2.1 mmol) of phenyl 4-phenylbutyl carbonate in 10 ml of pyridine was stirred at 100° C. overnight. The reaction mixture was poured into aqueous sodium hydroxide and extracted with ethyl acetate 3 times. The combined organic layer was dried over anhydrous magnesium sulfate; 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 5-(4-phenylbutoxycarbonyl)-4,5,6,7-tetrahydrofuro[3,2-c]pyridine as a mixture with phenol.

Workup

  1. extractionextracted with ethyl acetate 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. customThe resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=15/1 to 9/1)

Sources & evidence

ORD record
ord-3f9e8d76e50345818bd81a0aec93f274
Source dataset
uspto-grants-1999_12
Patent number
US05998433

Reaction notes

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