Sodium Methoxide → 6-Chloro-3-hydroxy-1-benzofuran-2-carbonitrile

HRID 904805Notes

Reaction equation

HRID 904805 reaction equation
[C:1]([C:5]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:6]=1[O:7][CH2:8][C:9]#[N:10])(OC)=[O:2].C[O-].[Na+]>C1C=CC=CC=1>[Cl:15][C:12]1[CH:13]=[CH:14][C:5]2[C:1]([OH:2])=[C:8]([C:9]#[N:10])[O:7][C:6]=2[CH:11]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 13282134Methyl 4-chloro-2-(cyanomethoxy)benzoate

Product 1

HCID 132821406-Chloro-3-hydroxy-1-benzofuran-2-carbonitrileYield 98.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 2-(2-carbomethoxy-5-chlorophenoxy)acetonitrile (22.6 g, 0.1 mol, described in Example 2) and sodium methoxide (0.2 mol, prepared from 4.6 g sodium metal and 50 mL dry methanol) in benzene (400 mL) was stirred and refluxed for 2 hr. After cooling, the precipitate was collected and dissolved in water. The solution was acidified with concentrated hydrochloric acid. The precipitate was extracted into diethyl ether and the solution was dried and evaporated. The solid residue was triturated with petroleum ether and gave 19.0 g of the title compound: mp ca 205° C., and NMR (DMSO-d6) δ7.6 (3H,m), and 11.4 (1H, broad).

Workup

  1. temperaturerefluxed for 2 hr
  2. temperatureAfter cooling
  3. customthe precipitate was collected
  4. dissolutiondissolved in water
  5. extractionThe precipitate was extracted into diethyl ether
  6. customthe solution was dried
  7. customevaporated
  8. customThe solid residue was triturated with petroleum ether

Sources & evidence

ORD record
ord-0efdb79ccbdb436f8f6bcd0e86d4d0e2
Source dataset
uspto-grants-1983_12
Patent number
US04420476

Reaction notes

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