4-(3-Pyridylhydroxymethyl)phenol hydrochloride → 4-(3-Pyridylmethyl)phenol hydrochloride

HRID 1680030Notes

Reaction equation

HRID 1680030 reaction equation
[ClH:1].[N:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH:8](O)[C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[CH:3]=1>[Pd].C(O)(=O)C>[ClH:1].[N:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[CH:3]=1

Participants

4

Reactant 1

HCID 132901344-(3-Pyridylhydroxymethyl)phenol hydrochloride

Product 1

HCID 132901364-(3-Pyridylmethyl)phenol hydrochlorideYield 11.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

Under an atmosphere of hydrogen, a mixture of 1.9 g of the hydroxymethyl compound (prepared as described in Example 8), 1.0 g of 5% palladium on carbon and 12 ml of acetic acid was stirred at room temperature for 24 hours, and filtered. The filtrate was concentrated under reduced pressure. The residue was dissolved in water, neutralized with sodium bicarbonate, extracted with diethyl ether, and the extract was concentrated under reduced pressure. After addition of 6 N hydrochloric acid to the residue, the solution was concentrated under reduced pressure. The residue was purified by recrystallization from ethanol-diethyl ether to give 0.204 g of the title compound having the following physical characteristics:

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in water
  4. extractionextracted with diethyl ether
  5. concentrationthe extract was concentrated under reduced pressure
  6. additionAfter addition of 6 N hydrochloric acid to the residue
  7. concentrationthe solution was concentrated under reduced pressure
  8. customThe residue was purified by recrystallization from ethanol-diethyl ether

Sources & evidence

ORD record
ord-112b889a83fe4d0f988c0bba84374ce2
Source dataset
uspto-grants-1981_06
Patent number
US04271170

Reaction notes

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