Sodium Hydroxide → HCID 13851426, compound

HRID 979169Notes

Reaction equation

HRID 979169 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[S:10][CH2:11][CH2:12][C:13]([OH:15])=O.[OH-].[Na+]>C(Cl)(Cl)Cl>[CH3:9][O:8][C:6]1[CH:7]=[C:2]([CH3:1])[C:3]2[S:10][CH2:11][CH2:12][C:13](=[O:15])[C:4]=2[CH:5]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13851425HCID 13851425, compound

Product 1

HCID 13851426HCID 13851426, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 21.1 g 3-[(2-methyl-4-methoxyphenyl)thio]propanoic acid and 160 g polyphosphoric ester in 150 ml CHCl3 is refluxed for 45 min. To the cooled reaction mixture is added 200 ml 0.5 N NaOH. The organic phase is separated and the aqueous phase is extracted with 100 ml CHCl3. The combined organic extracts are dried over Na2SO4, filtered, concentrated under reduced pressure and flash chromatrographed with ethyl acetate/hexane (8:92) to yield 6-methoxy-8-methyl-2H-[1]benzothiopyran-4-one.

Workup

  1. customTo the cooled reaction mixture
  2. customThe organic phase is separated
  3. extractionthe aqueous phase is extracted with 100 ml CHCl3
  4. dry with materialThe combined organic extracts are dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure and flash

Sources & evidence

ORD record
ord-61e2149a19f14ec29612012cdcb98da1
Source dataset
uspto-grants-1987_05
Patent number
US04666916

Reaction notes

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