Water → HCID 15316629, compound

HRID 981717Notes

Reaction equation

HRID 981717 reaction equation
[CH2:1]([S:8][CH2:9][CH2:10][C:11](=[O:24])[CH:12]([C:16](=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)C(=O)C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[O-].[Na+].O.OS(O)(=O)=O>C(OCC)C>[CH2:1]([S:8][CH2:9][CH2:10][C:11](=[O:24])[CH2:12][C:16]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:23])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 10942334Sodium MethoxideHCID 20070566HCID 20070566, compound

Product 1

HCID 15316629HCID 15316629, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

34.0 g (0.1 mol) of 1-benzylthio-4-benzoyl-3,5-hexanedione (see Example 17) are initially placed in a 100 ml flask equipped with a thermometer, a stirrer, a dropping funnel and a reflux condenser. 19.8 g (0.11 mol) of sodium methylate solution (30% in methanol) are added dropwise, with stirring, in the course of 40 minutes. In the course of this the reaction temperature rises from room temperature to approx. 32° C. The mixture is stirred for a further hour at room temperature and for a further 3 hours at approx. 45° C. and is then cooled to room temperature and stirred into 200 ml of water and 12 g of concentrated H2SO4. 180 ml of diethyl ether are added and the organic phase is separated off. The aqueous phase is washed with a further 50 ml of diethyl ether. The combined organic phases are washed with water, sodium bicarbonate and water again and are then dried, concentrated and fractionated. The resulting product, which has a boiling point of 180°-183° C. at 0.001 bar, is recrystallized from 20 ml of isopropanol.

Workup

  1. customequipped with a thermometer, a stirrer, a dropping funnel and a reflux condenser
  2. customrises from room temperature to approx. 32° C
  3. stirringThe mixture is stirred for a further hour at room temperature and for a further 3 hours at approx. 45° C.
  4. customthe organic phase is separated off
  5. washThe aqueous phase is washed with a further 50 ml of diethyl ether
  6. washThe combined organic phases are washed with water, sodium bicarbonate and water again
  7. customare then dried
  8. concentrationconcentrated
  9. customis recrystallized from 20 ml of isopropanol

Sources & evidence

ORD record
ord-9504ee4a10c24f41947417883b0aac31
Source dataset
uspto-grants-1991_02
Patent number
US04992504

Reaction notes

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