Acetic Anhydride → HCID 20205013, compound

HRID 978072Notes

Reaction equation

HRID 978072 reaction equation
C([C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[S:11][CH:12]([CH2:16][CH2:17][CH2:18][CH3:19])[C:13]([OH:15])=O)(O)=O.[C:20]([O-])(=[O:22])[CH3:21].[Na+].C(OC(=O)C)(=O)C>O>[C:20]([O:15][C:13]1[C:6]2[CH:7]=[C:8]([Cl:10])[CH:9]=[CH:4][C:5]=2[S:11][C:12]=1[CH2:16][CH2:17][CH2:18][CH3:19])(=[O:22])[CH3:21]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 20205019HCID 20205019, compound

Product 1

HCID 20205013HCID 20205013, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-(2'-carboxy-4'-chlorophenylthio)hexanoic acid (2.3 g, 7.6 mmol), anhydrous sodium acetate (1.0 g), and acetic anhydride (5 ml) was heated at 80° C. for 30 minutes. After gas evolution had ceased, the temperature was gradually raised to 120° C. which was maintained for 30 minutes. The cooled reaction mixture was then poured into water and extracted with diethyl ether. The combined ethereal extracts were washed with 1% aqueous sodium hydroxide solution, water, and saturated aqueous sodium chloride solution, dried (sodium sulfate) and evaporated. The residue was vacuum filtered through a pad of silica gel (Merck No. 7734) eluting with 25:1 hexane-ether to give 3-acetoxy-2-butyl-5-chlorobenzo[b]thiophene as a colorless oil; yield 1.1 g (40% overall from the 2-step sequence), m/z 282 (M+.).

Workup

  1. temperaturethe temperature was gradually raised to 120° C. which
  2. temperaturewas maintained for 30 minutes
  3. customThe cooled reaction mixture
  4. extractionextracted with diethyl ether
  5. washThe combined ethereal extracts were washed with 1% aqueous sodium hydroxide solution, water, and saturated aqueous sodium chloride solution
  6. dry with materialdried (sodium sulfate)
  7. customevaporated
  8. filtrationfiltered through a pad of silica gel (Merck No
  9. wash7734) eluting with 25:1 hexane-ether

Sources & evidence

ORD record
ord-d130f07c5ca2486588776f800e9544da
Source dataset
uspto-grants-1987_05
Patent number
US04663344

Reaction notes

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