Acetic Acid → 3-n-Hexyl-7-(o-tolylthio)-2,3-dihydrobenzofuran-2-one

HRID 1164123Notes

Reaction equation

HRID 1164123 reaction equation
C([C:3]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([S:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[CH3:28])[C:16]=1OC)([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]C)[C:4]([O:6]CC)=[O:5])#N.[C:31](O)(=O)C>I>[CH2:9]([CH:3]1[C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([S:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[CH3:28])[C:16]=2[O:6][C:4]1=[O:5])[CH2:10][CH2:11][CH2:12][CH2:13][CH3:31]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 20513448Ethyl 2-cyano-2-[2-methoxy-3-(o-tolylthio)phenyl]octanoate

Product 1

HCID 205134193-n-Hexyl-7-(o-tolylthio)-2,3-dihydrobenzofuran-2-one

Reagents, catalysts & solvents 1

HCID 24841Hydrogen iodideSolvent

Procedure

A solution of ethyl 2-cyano-2-[2-methoxy-3-(o-tolylthio)phenyl]octanoate (5 g) in hydriodic acid (58%, 20 ml) and acetic acid (40 ml) was refluxed under heating for 24 hours. The reaction mixture was treated in a similar manner to that of Example 31-(7) to give oily 3-n-hexyl-7-(o-tolylthio)-2,3-dihydrobenzofuran-2-one (1.7 g).

Workup

  1. temperatureunder heating for 24 hours
  2. additionThe reaction mixture was treated in a similar manner to that of Example 31-(7)

Sources & evidence

ORD record
ord-0ef6db4445084c569edf0fe855a1bd86
Source dataset
uspto-grants-1983_01
Patent number
US04367238

Reaction notes

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