Hydrochloric Acid → 4-(Benzyloxy)pyridin-3-ol

HRID 1862274Notes

Reaction equation

HRID 1862274 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]=[CH:11][C:10]=1[O:15]COC)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C(=O)(O)[O-].[Na+]>>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]=[CH:11][C:10]=1[OH:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 186191724-Benzyloxy-3-methoxymethoxypyridine

Product 1

HCID 186192064-(Benzyloxy)pyridin-3-olYield 95.3%

Conditions

Temperature
60 °C

Procedure

A mixture of 0.7 g of 4-benzyloxy-3-methoxymethoxypyridine and 1N hydrochloric acid was stirred for 2 hours at 60° C. The mixture was poured into saturated aqueous sodium bicarbonate solution, extracted with ethyl acetate. The organic layer is washed with saturated saline, dried over anhydrous magnesium sulfate, concentrated to obtain 0.547 g of 4-benzyloxy-3-hydroxypyridine.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer is washed with saturated saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-331f82de50ac43bbaaf12280a2691e1b
Source dataset
uspto-grants-2003_03
Patent number
US06537948B1

Reaction notes

Loading…