Catechol → Methyl 1,3-benzodioxole-2-carboxylate

HRID 455527Notes

Reaction equation

HRID 455527 reaction equation
[C:1]1([C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4])[OH:2].C[O-].[Na+].Cl[CH:13](Cl)[C:14]([O:16][CH3:17])=[O:15].Cl>CO.O>[CH3:17][O:16][C:14]([CH:13]1[O:4][C:3]2[CH:5]=[CH:6][CH:7]=[CH:8][C:1]=2[O:2]1)=[O:15]

Participants

7

Reactant 4

HCID 289CatecholHCID 313Hydrochloric AcidHCID 8315Methyl dichloroacetateHCID 10942334Sodium Methoxide

Product 1

HCID 578017Methyl 1,3-benzodioxole-2-carboxylate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Catechol (10.26 g, 93.2 mmol), sodium methoxide (25% by weight in methanol, 40.3 g, 186 mmol), and methyl dichloroacetate (13.3 g, 93.2 mmol) were combined in dry methanol (100 mL). The solution was heated to reflux overnight. The reaction was cooled to room temperature, acidified by addition of concentrated hydrochloric acid and then reduced in volume under vacuum to about 50 mL. Water was added and the mixture was extracted with diethyl ether (3×100 mL). The combined organic solution was dried with MgSO4, concentrated to a brown solid, and chromatographed (2% ethyl acetate in hexane) to yield benzo[1,3]dioxole-2-carboxylic acid methyl ester as a colorless oil.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux overnight
  3. extractionthe mixture was extracted with diethyl ether (3×100 mL)
  4. dry with materialThe combined organic solution was dried with MgSO4
  5. concentrationconcentrated to a brown solid
  6. customchromatographed (2% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-cd045ec77e8f4f6f8ae0fffcf2e1acc9
Source dataset
uspto-grants-2013_07
Patent number
US08497298B2

Reaction notes

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