Water → HCID 86743543, compound

HRID 476602Notes

Reaction equation

HRID 476602 reaction equation
[CH3:1][CH2:2][O-:3].[Na+].O[CH:6]=[C:7]1[C:16](=[S:17])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH3:18])[CH:14]=2)[O:9][CH:8]1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O.C(Cl)(Cl)Cl>C(O)C.C(O)(=O)C>[CH2:2]([O:3][CH:6]=[C:7]1[C:16](=[S:17])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH3:18])[CH:14]=2)[O:9][CH:8]1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH3:1]

Participants

7

Reactant 4

HCID 962WaterHCID 6212ChloroformHCID 2723922Sodium ethoxideHCID 178422546HCID 178422546, compound

Product 1

HCID 86743543HCID 86743543, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent2×

Procedure

A solution of 5.5 g sodium ethylate in 40 ml absolute ethanol is added to a suspension of 29.5 g 3-hydroxymethylidene-6-methyl-thioflavanone in 400 ml absolute ethanol. After stirring for one day at room temperature the suspension is poured into a mixture of water and chloroform containing acetic acid. The organic layer is separated and the aqueous layer is extracted with chloroform. The combined organic extracts are washed with water, dried over magnesium sulfate, filtered and evaporated. The residue is recrystallised from a mixture of light petroleum and chloroform. Pure 3-ethoxymethylidene-6-methyl-thioflavanone is obtained as yellow crystals; m.p. 140°-142° C.

Workup

  1. customThe organic layer is separated
  2. extractionthe aqueous layer is extracted with chloroform
  3. washThe combined organic extracts are washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is recrystallised from a mixture of light petroleum and chloroform

Sources & evidence

ORD record
ord-7ebadc9030fa413bb36de4c96cc4e68b
Source dataset
uspto-grants-1989_12
Patent number
US04885298

Reaction notes

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