Water → 2-Methyl-3-hydroxy-4-benzoylthiomethyl-5-vinylpyridine

HRID 461081Notes

Reaction equation

HRID 461081 reaction equation
[CH3:1][C:2]1[C:7]([OH:8])=[C:6]([CH2:9]Cl)[C:5]([CH:11]=[CH2:12])=[CH:4][N:3]=1.[C:13]([O-:21])(=[S:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[K+].O>C(O)C>[CH3:1][C:2]1[C:7]([OH:8])=[C:6]([CH2:9][S:20][C:13](=[O:21])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:5]([CH:11]=[CH2:12])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 202639602-Methyl-3-hydroxy-4-chloromethyl-5-vinylpyridineHCID 23681850Potassium thiobenzoate

Product 1

HCID 202640282-Methyl-3-hydroxy-4-benzoylthiomethyl-5-vinylpyridine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 65 g. of 2-methyl-3-hydroxy-4-chloromethyl-5-vinylpyridine in 1 liter of ethanol under nitrogen there was added 96 g. of potassium thiobenzoate in 200 ml. of water over 30 minutes. After 1 hour, the ethanol was evaporated at 40° C. and the aqueous solution was extracted with 4 × 300 ml. of ethyl acetate. The extract was washed with 1 × 75 ml. of water, dried over magnesium sulfate and concentrated to dryness to give 2-methyl-3-hydroxy-4-benzoylthiomethyl-5-vinylpyridine.

Workup

  1. customthe ethanol was evaporated at 40° C.
  2. extractionthe aqueous solution was extracted with 4 × 300 ml
  3. washThe extract was washed with 1 × 75 ml
  4. dry with materialof water, dried over magnesium sulfate
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-72c8a8db770b4f1ab65df28f23da9588
Source dataset
uspto-grants-1977_12
Patent number
US04061759

Reaction notes

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