Toluene → HCID 20070564, compound

HRID 981718Notes

Reaction equation

HRID 981718 reaction equation
C[O-:2].[Na+].[CH3:4][C:5](=[O:10])[C:6]([CH3:9])([CH3:8])[CH3:7].[CH2:11]([CH2:17][C:18](OC)=[S:19])[CH2:12][CH2:13][CH2:14]CC.[C:22]1([CH3:28])C=CC=CC=1>>[CH2:18]([S:19][CH2:28][C:22](=[O:2])[CH2:4][C:5](=[O:10])[C:6]([CH3:9])([CH3:8])[CH3:7])[CH2:17][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 4

HCID 1140TolueneHCID 6416PinacoloneHCID 10942334Sodium MethoxideHCID 11423867HCID 11423867, compound

Product 1

HCID 20070564HCID 20070564, compound

Conditions

Temperature
106 °C

Procedure

250 ml of toluene and 99 g (0.55 mol) of sodium methylate solution (30% in methanol) are initially placed in a flask equipped with a thermometer, a stirrer, a dropping funnel and a distillation bridge with receiver, and 108.4 g of a methanol/toluene mixture are distilled off until the reaction temperature reaches 109° C. 60 g (0.6 mol) of pinacolone are then added dropwise at the same temperature and 95 g (0.5 mol) of methyl n-hexylthioacetate are added dropwise in the course of 20 minutes. In the course of this a further 32.5 g of a methanol/toluene mixture are distilled off. The mixture is then stirred for a further 35 minutes at 106° C. and is worked up analogously to Example 18. The residue is concentrated and then fractionated in vacuo.

Workup

  1. customequipped with a thermometer, a stirrer, a dropping funnel
  2. distillationa distillation bridge with receiver, and 108.4 g of a methanol/toluene mixture are distilled off until the reaction temperature
  3. customreaches 109° C
  4. additionare added dropwise in the course of 20 minutes
  5. distillationIn the course of this a further 32.5 g of a methanol/toluene mixture are distilled off
  6. concentrationThe residue is concentrated

Sources & evidence

ORD record
ord-8c32c1b3e46c45e9b0953c8793bcbf78
Source dataset
uspto-grants-1991_02
Patent number
US04992504

Reaction notes

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