Methanol → HCID 86677617, compound

HRID 1967604Notes

Reaction equation

HRID 1967604 reaction equation
CO.[C:3]([O-])(=[S:5])[CH3:4].[K+].[C:8]([C:12]1[CH:17]=[CH:16][C:15]([CH:18](Br)[C:19]([O:21][CH3:22])=[O:20])=[CH:14][CH:13]=1)([CH3:11])([CH3:10])[CH3:9].CCCCCCC>O>[C:3]([CH:18]([C:15]1[CH:16]=[CH:17][C:12]([C:8]([CH3:11])([CH3:10])[CH3:9])=[CH:13][CH:14]=1)[C:19]([O:21][CH3:22])=[O:20])(=[S:5])[CH3:4]

Participants

6

Reactant 4

HCID 887Methanol3×HCID 8900HeptaneHCID 12717581HCID 12717581, compoundHCID 23670855Potassium ethanethioate

Product 1

HCID 86677617HCID 86677617, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
35 °C

Procedure

To a methanol (203 g) solution of potassium thioacetate (70.4 g, 0.616 mol, 1.3 equivalent amounts based on the starting material), a mixed solution of a 33 mass % methanol solution (408.5 g, 0.473 mol) of methyl 2-(4-t-butylphenyl)-2-bromoacetate and methanol (270 g) was dropwise added over a period of 1 hour and 20 minutes, followed by stirring at from 30 to 40° C. for 1 hour. Then, the reaction solution was mixed with heptane (674 g) and water (675 g) and stirred for 20 minutes, followed by liquid separation. The solvent was distilled off from the obtained organic layer under reduced pressure at 40° C. until the total amount became 382 g. The obtained solution was cooled to 30° C. over a period of 1 hour, and 0.13 g of seed crystals were added. Then, the solution was stirred for 1 hour and further cooled to −10° C. over a period of 3 hours. Then, the solution was stirred for 1 hour and subjected to filtration, and the obtained crystals were dried to give the desired product (110.7 g, yield: 83.3%).

Workup

  1. additionwas dropwise added over a period of 1 hour and 20 minutes
  2. stirringstirred for 20 minutes
  3. customfollowed by liquid separation
  4. distillationThe solvent was distilled off from the obtained organic layer under reduced pressure at 40° C. until the total amount
  5. temperatureThe obtained solution was cooled to 30° C. over a period of 1 hour
  6. addition0.13 g of seed crystals were added
  7. stirringThen, the solution was stirred for 1 hour
  8. temperaturefurther cooled to −10° C. over a period of 3 hours
  9. stirringThen, the solution was stirred for 1 hour
  10. filtrationsubjected to filtration
  11. customthe obtained crystals were dried

Sources & evidence

ORD record
ord-b87cf7c6341e484b8cf416f1c648a36a
Source dataset
uspto-grants-2013_04
Patent number
US08420849B2

Reaction notes

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