Hydrochloric Acid → 2-Methyl-3-hydroxy-4-mercaptomethyl-5-vinylpyridine

HRID 614422Notes

Reaction equation

HRID 614422 reaction equation
[CH3:1][C:2]1[C:7]([OH:8])=[C:6]([CH2:9][S:10]C(=O)C2C=CC=CC=2)[C:5]([CH:19]=[CH2:20])=[CH:4][N:3]=1.[OH-].[Na+].Cl.C(=O)(O)[O-].[Na+]>O1CCCC1>[CH3:1][C:2]1[C:7]([OH:8])=[C:6]([CH2:9][SH:10])[C:5]([CH:19]=[CH2:20])=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 202640282-Methyl-3-hydroxy-4-benzoylthiomethyl-5-vinylpyridine

Product 1

HCID 130669462-Methyl-3-hydroxy-4-mercaptomethyl-5-vinylpyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1 g. of 2-methyl-3-hydroxy-4-benzoylthiomethyl-5-vinylpyridine, 10 ml. of tetrahydrofuran, and 10 ml. of 2.5 N aqueous sodium hydroxide was aged at room temperature overnight. The solution was acidified to about pH 6 with hydrochloric acid and then adjusted to pH 7.5 with solid sodium bicarbonate. The mixture was extracted with 3 × 100 ml. of ethyl acetate: isopropanol (9:1 v/v). The extract was dried over magnesium sulfate and concentrated to give 2-methyl-3-hydroxy-4-mercaptomethyl-5-vinylpyridine.

Workup

  1. additionA mixture of 1 g
  2. extractionThe mixture was extracted with 3 × 100 ml
  3. dry with materialThe extract was dried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9db0076e0e59409e86e4d10d700d02a8
Source dataset
uspto-grants-1979_03
Patent number
US04144342

Reaction notes

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