Hydrochloric Acid → 4-(Pyridin-4-yl)phenol

HRID 393282Notes

Reaction equation

HRID 393282 reaction equation
C1(C[O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)=[CH:11][CH:10]=2)C=CC=CC=1.Cl>CO.[OH-].[OH-].[Pd+2]>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:16]=[CH:17][N:18]=[CH:19][CH:20]=2)=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 226488624-(4-(Benzyloxy)phenyl)pyridine

Product 1

HCID 1354101774-(Pyridin-4-yl)phenolYield 88%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A solution 4-[4-(phenylmethoxy)phenyl]pyridine (120 mg, 0.46 mmol), Pd(OH)2/C (20% w/w, 10 mg) and aqueous 1.0 M HCl solution (0.5 mL) in MeOH (20 mL) was stirred under a hydrogen atmosphere (50 psi) for 17 h at 25° C. The catalyst was removed by filtration, Et3N (0.1 mL) was added and the filtrate was concentrated under reduced pressure. The residue was treated with hot THF. The resulting suspension was filtered and the filtrate concentrated under reduced pressure to give the title compound (69 mg, 88% yield) as a beige solid.

Workup

  1. customThe catalyst was removed by filtration, Et3N (0.1 mL)
  2. additionwas added
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionThe residue was treated with hot THF
  5. filtrationThe resulting suspension was filtered
  6. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-f2810b0d580f4173b74822a9706d8e60
Source dataset
uspto-grants-2004_10
Patent number
US06806265B2

Reaction notes

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