Water → HCID 54239271, compound

HRID 1194819Notes

Reaction equation

HRID 1194819 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](CC(O)=O)[CH:9]=2)=[O:7])=[CH:4][CH:3]=1.ClC1C(=O)C(C#N)=C(C#N)[C:28](=[O:31])[C:29]=1Cl.[OH2:37].O1CCO[CH2:40][CH2:39]1>>[C:28]([O:31][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][C:14]([CH2:39][CH3:40])=[CH:13][C:12]=2[CH:11]=1)(=[O:37])[CH3:29]

Participants

5

Reactant 4

HCID 962WaterHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 312751,4-DioxaneHCID 21268644HCID 21268644, compound

Product 1

HCID 54239271HCID 54239271, compound

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-16a2972879c344279284c8a8358e30bc
Source dataset
uspto-grants-1989_03
Patent number
US04816473

Reaction notes

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