Pyridine → 2-(n-Octylthio)ethyl methacrylate

HRID 1732675Notes

Reaction equation

HRID 1732675 reaction equation
[CH2:1]([S:9][CH2:10][CH2:11][OH:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].N1C=CC=CC=1.[C:19](Cl)(=[O:23])[C:20]([CH3:22])=[CH2:21]>C1C=CC=CC=1>[C:19]([O:12][CH2:11][CH2:10][S:9][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])(=[O:23])[C:20]([CH3:22])=[CH2:21]

Participants

5

Reactant 3

HCID 1049PyridineHCID 13528Methacryloyl chlorideHCID 190792-(Octylthio)ethanol

Product 1

HCID 203044782-(n-Octylthio)ethyl methacrylateYield 66.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
5 °C

Procedure

2(n-Octylthio)ethanol (13.10 grams, 0.0688 mole) and anhydrous pyridine (65.5 grams) were charged to a three-necked flask fitted with a condenser protected with a drying tube, dropping funnel, thermometer and magnetic stirrer. The solution was cooled to 5° C., and methacrylyl chloride (7.20 grams, 0.0688 mole) was then added dropwise over a 26-minute period. The reaction solution was maintained at 9°-11° C. throughout the addition period, and then at 25° C. for another three hours with stirring. The reaction mixture was then diluted with 150 ml of benzene, and the pyridine hydrochloride present was removed by filtration. The filtrate was washed twice with dilute hydrochloric acid, then with water until neutral and finally dried over anhydrous sodium sulfate. The benzene solvent was stripped off leaving 13.1 grams of crude product which was purified by vacuum distillation to yield 11.8 grams of the desired ester with a boiling point of 111°-124° C./0.07 mm in a yield of 66%.

Workup

  1. customfitted with a condenser
  2. customprotected with a drying tube
  3. temperatureThe reaction solution was maintained at 9°-11° C. throughout the addition period
  4. customthe pyridine hydrochloride present was removed by filtration
  5. washThe filtrate was washed twice with dilute hydrochloric acid
  6. dry with materialwith water until neutral and finally dried over anhydrous sodium sulfate
  7. customleaving 13.1 grams of crude product which
  8. distillationwas purified by vacuum distillation

Sources & evidence

ORD record
ord-ff1fafafff7a4f6ca399b0088fb54722
Source dataset
uspto-grants-1980_12
Patent number
US04238575

Reaction notes

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