Water → HCID 21287556, compound

HRID 868624Notes

Reaction equation

HRID 868624 reaction equation
[CH3:1][C:2]1[CH:22]=[CH:21][C:5]([C:6]([C:8]2[C:16]3[O:15][CH2:14][CH2:13][C:12]=3[CH:11]=[C:10]([CH2:17][C:18]([OH:20])=[O:19])[CH:9]=2)=[O:7])=[CH:4][CH:3]=1.Cl[C:24]1C(=O)C(C#N)=C(C#N)C(=O)[C:29]=1Cl.O>O1CCOCC1>[CH2:24]([O:19][C:18](=[O:20])[CH2:17][C:10]1[CH:9]=[C:8]([C:6](=[O:7])[C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:22][CH:21]=2)[C:16]2[O:15][CH:14]=[CH:13][C:12]=2[CH:11]=1)[CH3:29]

Participants

5

Reactant 3

HCID 962WaterHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 21268644HCID 21268644, compound

Product 1

HCID 21287556HCID 21287556, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

7-(4-Methylbenzoyl)-2,3-dihydrobenzofuran-5-ylacetic acid (1.0 g) was dissolved in dioxane (20 ml). To this was added 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) (1.2 g) and the solution heated at reflux for 1 hour. The reaction mixture was added to water and extracted with ethyl acetate, dried with magnesium sulfate and evaporated to dryness. The residue was run on a silica gel column eluting with ethyl acetate/hexane to give ethyl(7-(4-methylbenzoyl)-benzofuran-5-yl)acetate. The acetate was hydrolyzed by the same method set out in Example 3 to give (7-(4-methylbenzoyl)benzofuran-5-yl)acetic acid melting points. This method is especially useful when the 2,3-dihydro starting material contains an alkyl group.

Workup

  1. temperaturethe solution heated
  2. temperatureat reflux for 1 hour
  3. extractionextracted with ethyl acetate
  4. dry with materialdried with magnesium sulfate
  5. customevaporated to dryness
  6. washeluting with ethyl acetate/hexane

Sources & evidence

ORD record
ord-0d260574acb34a8d8839287ae4aa6ee1
Source dataset
uspto-grants-1988_10
Patent number
US04780480

Reaction notes

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