Acetic Anhydride → HCID 20205036, compound

HRID 978081Notes

Reaction equation

HRID 978081 reaction equation
[C:1]1([CH:7]([S:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[C:13]=2[C:19]([OH:21])=O)C(O)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:22]([O-:25])(=O)[CH3:23].[Na+].[C:27](OC(=O)C)(=[O:29])[CH3:28]>>[C:27]([O:21][C:19]1[C:13]2[C:14]([O:18][C:22](=[O:25])[CH3:23])=[CH:15][CH:16]=[CH:17][C:12]=2[S:11][C:7]=1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)(=[O:29])[CH3:28]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 20205054HCID 20205054, compound

Product 1

HCID 20205036HCID 20205036, compound

Conditions

Temperature
60 °C

Procedure

A mixture of 2-phenyl-2-(2'-carboxy-3'-hydroxyphenylthio)-acetic acid (0.19 g, 0.62 mmol), sodium acetate (0.38 g) and acetic anhydride (2 ml) was heated at 60° C. for 10 minutes, with vigorous gas evolution taking place. The mixture was poured into ice-water and extracted with diethyl ether. The combined organic extracts were washed with 1% aqueous sodium hydroxide, water, dried (sodium sulfate), and evaporated. The residue was subjected to chromatography and evaporated. The residue was subjected to chromatography on a column of silica gel (Merck No. 7734), eluting with 1:1 hexane-ether to afford 3,4-diacetoxy-2-phenylbenzo[b]thiophene as a white solid; yield 29 mg (14%); m/z 326 (M+.).

Workup

  1. extractionextracted with diethyl ether
  2. washThe combined organic extracts were washed with 1% aqueous sodium hydroxide, water
  3. dry with materialdried (sodium sulfate)
  4. customevaporated
  5. customevaporated
  6. wash7734), eluting with 1:1 hexane-ether

Sources & evidence

ORD record
ord-b03c588c896b4281bf63b67729216b5a
Source dataset
uspto-grants-1987_05
Patent number
US04663344

Reaction notes

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