Sodium ethoxide → Ethyl 7-hydroxy-1,4-benzodioxin-2-carboxylate

HRID 1756029Notes

Reaction equation

HRID 1756029 reaction equation
C([O-])C.[Na+].C([O:8][C:9]1[CH:10]=[CH:11][C:12]2[O:17][CH:16]=[C:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[O:14][C:13]=2[CH:23]=1)(=O)C>C(O)C>[OH:8][C:9]1[CH:10]=[CH:11][C:12]2[O:17][CH:16]=[C:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[O:14][C:13]=2[CH:23]=1

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 10956401Ethyl 7-acetoxy-1,4-benzodioxin-2-carboxylate

Product 1

HCID 15372688Ethyl 7-hydroxy-1,4-benzodioxin-2-carboxylateYield 96%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Add 0.5 cm3 of a molar solution of sodium ethanolate in ethanol to a solution of 1 g (3.78 mmol) of ethyl 7-acetoxy-1,4-benzodioxin-2-carboxylate in 15 cm3 of anhydrous ethanol under a nitrogen atmosphere. Stir for 18 hours at room temperature and then neutralise with Dowex X-8 resin, acid form, which has been washed beforehand with ethanol. After filtration and concentration to dryness under partial pressure, the crude product obtained is purified by chromatography on a silica column (eluant: petroleum ether/diethyl ether, 80:20). Ethyl 7-hydroxy-1,4-benzodioxin-2-carboxylate is thereby obtained in a yield of 96%. Melting point: 160° C. ##STR43##

Workup

  1. washhas been washed beforehand with ethanol
  2. filtrationAfter filtration and concentration to dryness under partial pressure
  3. customthe crude product obtained
  4. customis purified by chromatography on a silica column (eluant: petroleum ether/diethyl ether, 80:20)

Sources & evidence

ORD record
ord-276591cfc6f04d8b810f8e4062628bef
Source dataset
uspto-grants-1995_08
Patent number
US05439909

Reaction notes

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