Hydrochloric Acid → HCID 12215669, compound

HRID 1248927Notes

Reaction equation

HRID 1248927 reaction equation
C[O:2][C:3]([CH2:5][S:6][CH:7]([CH:11]([CH3:13])[CH3:12])[C:8](=[O:10])[CH3:9])=O.C[O-].[Na+].Cl>C1(C)C=CC=CC=1>[CH:11]([CH:7]1[C:8](=[O:10])[CH2:9][C:3](=[O:2])[CH2:5][S:6]1)([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 12215668Acetic acid, [(1-acetyl-2-methylpropyl)thio]-, methyl ester

Product 1

HCID 12215669HCID 12215669, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

204 g (1 mol) of 3-methoxycarbonylmethylthio-4-methyl-2-pentanone are added dropwise within one hour, at 0° C. with vigorous stirring, to a suspension of 108 g (2 mol) of freshly prepared sodium methylate in 2 liters of absolute toluene. The reaction mixture is stirred at 0° C. for a further 30 minutes, then poured into a mixture of 200 ml of concentrated hydrochloric acid and 800 ml of ice-water, and the organic phase is separated off, and the aqueous phase is extracted three times with dichloromethane. The combined organic phases are concentrated to 500 ml in vacuo and extracted with 500 ml of ice-cold 4N sodium hydroxide solution. The aqueous extracts are immediately acidified with a total of 400 ml of ice-cold hydrochloric acid and extracted three times with 200 ml of dichloromethane each time. The combined dichloromethane phases are dried over sodium sulphate and the solvent is removed in vacuo. The remaining solid is recrystallized from ligroin/ethanol. 150 g (87% of theory) of 2-isopropyltetrahydrothiopyran-3,5-dione of melting point 71° C. are obtained. ##STR53##

Workup

  1. customthe organic phase is separated off
  2. extractionthe aqueous phase is extracted three times with dichloromethane
  3. concentrationThe combined organic phases are concentrated to 500 ml in vacuo
  4. extractionextracted with 500 ml of ice-cold 4N sodium hydroxide solution
  5. extractionextracted three times with 200 ml of dichloromethane each time
  6. dry with materialThe combined dichloromethane phases are dried over sodium sulphate
  7. customthe solvent is removed in vacuo
  8. customThe remaining solid is recrystallized from ligroin/ethanol

Sources & evidence

ORD record
ord-8687d1bae9474a8ea2f1f319dece9ce4
Source dataset
uspto-grants-1986_12
Patent number
US04628060

Reaction notes

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