Sodium Hydroxide → 7-Chloro-3(2H)-benzofuranone

HRID 330272Notes

Reaction equation

HRID 330272 reaction equation
C([C:5]1[O:6][C:7]2[C:14]([Cl:15])=[CH:13][CH:12]=[CH:11][C:8]=2[C:9]=1[OH:10])(OC)=O.[OH-].[Na+]>O1CCOCC1>[Cl:15][C:14]1[C:7]2[O:6][CH2:5][C:9](=[O:10])[C:8]=2[CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54735985HCID 54735985, compound

Product 1

HCID 148193417-Chloro-3(2H)-benzofuranoneYield 99.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

According to the procedure of D. C. Schroeder, et al., J Org. Chem., 27, 586 (1962) a mixture of 2-carbomethoxy-7-chloro-3-hydroxybenzofuran (16.9 g, 0.075 mol), dioxane 75 mL), and 1N NaOH (375 mL, 0.375 mol) was stirred at room temperature for 2 days. The dioxane was removed under reduced pressure and the mixture was left standing for another day. Acidification with 2N HCl (270 mL, slowly) and filtration of the resulting precipitate gave a yellow solid (12.6 g). NMR analysis showed this material to be a 3:1 mixture of product and starting material. Purification by preparative HPLC gave a yellow solid (5.8 g, 46%), m.p. 108°-111° C.

Workup

  1. customThe dioxane was removed under reduced pressure
  2. waitthe mixture was left
  3. waitstanding for another day
  4. filtrationAcidification with 2N HCl (270 mL, slowly) and filtration of the resulting precipitate

Sources & evidence

ORD record
ord-d417547eb6d74e008fa22d6a7ea35c50
Source dataset
uspto-grants-1990_01
Patent number
US04895860

Reaction notes

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