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Sulfuric Acid → 3-[(Methoxycarbonyl)methylthio]-2,6-dimethyl-4-heptanone

HRID 461220
Notes
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Reaction equation

HRID 461220 reaction equation
OS(O)(=O)=O.C[O-].[Na+].[SH:9][CH:10]([C:14](=[O:19])[CH2:15][CH:16]([CH3:18])[CH3:17])[CH:11]([CH3:13])[CH3:12].[CH3:20][O:21][C:22](=[O:25])[CH2:23]Cl>CO.O>[CH3:20][O:21][C:22]([CH2:23][S:9][CH:10]([C:14](=[O:19])[CH2:15][CH:16]([CH3:18])[CH3:17])[CH:11]([CH3:13])[CH3:12])=[O:25]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 7295Methyl chloroacetateHCID 10942334Sodium MethoxideHCID 205190993-Mercapto-2,6-dimethyl-4-heptanone

Product 1

HCID 227662283-[(Methoxycarbonyl)methylthio]-2,6-dimethyl-4-heptanone

Reagents, catalysts & solvents 2

HCID 887
Methanol
Solvent
2×
HCID 962WaterSolvent

Conditions

Temperature
24 °C

Procedure

Into a 50 ml, round-bottom, three-necked flask equipped with magnetic stirrer, pot thermometer, "Y" tube, nitrogen inlet tube, reflux condenser with cotton plug, H2SO4 bubbler for nitrogen, and cold water bath is added a solution of 0.65 grams of sodium methoxide dissolved in 10 ml anhydrous methanol. At a reaction mass temperature of 25°-28° C and over a period of one minute, with stirring, is added a solution of 2.1 grams of 3-mercapto-2,6-dimethyl-4-heptanone dissolved in 2 ml anhydrous methanol. After stirring 8 minutes, 1.30 grams of methylchloroacetate (0.012 moles) is added over a period of 2 minutes, to the reaction mass; the temperature of the reaction mass rising to 38° C. The reaction mass is allowed to cool to 24° C and is stirred for a period of 2 hours.

Workup

  1. customInto a 50 ml, round-bottom, three-necked flask equipped with magnetic stirrer
  2. stirringAfter stirring 8 minutes
  3. customrising to 38° C
  4. stirringis stirred for a period of 2 hours

Sources & evidence

ORD record
ord-d58a7c95ea8241028e252461118ddef2
Source dataset
uspto-grants-1977_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04061796

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes