2,3-Dihydroxybenzoic Acid → 2,3-Dihydro-1,4-benzodioxin-5-carboxylic acid

HRID 1462182Notes

Reaction equation

HRID 1462182 reaction equation
[OH:1][C:2]1[C:10]([OH:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].O=O.[OH-].[K+].Br[CH:17](Br)[CH3:18]>O.C(O)C>[CH2:17]1[CH2:18][O:11][C:10]2[C:2](=[C:3]([CH:7]=[CH:8][CH:9]=2)[C:4]([OH:6])=[O:5])[O:1]1

Participants

7

Reactant 4

HCID 192,3-Dihydroxybenzoic AcidHCID 977OxygenHCID 112011,1-DibromoethaneHCID 14797Potassium Hydroxide

Product 1

HCID 781842,3-Dihydro-1,4-benzodioxin-5-carboxylic acidYield 96.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

2,3-Dihydroxybenzoic acid (25 g, 0.16 mol) was heated under reflux in an oxygen-free atmosphere with potassium hydroxide (26.42 g, 0.47 mole) and dibromoethane (13.46 g, 0.07 mol) using 95% ethanol (60 ml) and water (142 ml as solvent as described in J. Org. Chem. (1948), 13, 489-95 to give 2,3-ethylenedioxybenzoic acid (12.2 g, 43%), m.pt. 195°-196° C.

Sources & evidence

ORD record
ord-611ebd0e598a4984b3023e430c73e3db
Source dataset
uspto-grants-1984_07
Patent number
US04459300

Reaction notes

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