Carbon Dioxide → 2,6-Dimethoxybenzoic Acid

HRID 231355

Reaction equation

HRID 231355 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[CH:4]=1.CN(C)CCN(C)C.C([N-]CC)C.[K+].[C:25](=[O:27])=[O:26]>C(N(CC)CC)C.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1[C:25]([OH:27])=[O:26]

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 90251,3-DimethoxybenzeneHCID 12552075Potassium diethylamide

Product 1

HCID 151092,6-Dimethoxybenzoic AcidYield 69%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8471TriethylamineSolvent2×

Procedure

A solution of 1,3-dimethoxybenzene (12.06 g.) and tetramethylethylenediamine (15 ml.) in triethylamine (20 ml.) was added to the potassium diethylamide reaction mixture and stirred for two hours. The entire mixture, a gray suspension, was poured into a 1-liter beaker containing crushed dry ice (456 g.) with the aid of 35 ml of added triethylamine and was allowed to warm to room temperature. The contents of the beaker were transferred into a 1-liter flask with the aid of some water. All volatile components were removed by a rotary evaporator. The solid remaining in the flask was partitioned between diethyl ether (30 ml.) and water, which was extracted with diethyl ether (four times, 30 ml.). The aqueous layer was acidified with concentrated hydrochloric acid to a pH of 1. The resultant precipitate was collected by filtration, water-washed and air dried to give 10.99 g. (69% yield) of 2,6-dimethoxybenzoic acid.

Workup

  1. additionThe entire mixture, a gray suspension, was poured into a 1-liter beaker
  2. additioncontaining
  3. customAll volatile components were removed by a rotary evaporator
  4. customwas partitioned between diethyl ether (30 ml.) and water, which
  5. extractionwas extracted with diethyl ether (four times, 30 ml.)
  6. filtrationThe resultant precipitate was collected by filtration, water-
  7. washwashed
  8. customair dried
  9. customto give 10.99 g

Sources & evidence

ORD record
ord-099de03743944935877b63130f78306e
Source dataset
uspto-grants-1989_07
Patent number
US04845276

Linked notes

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