Water → 1,4-Benzenediacetic acid, dimethyl ester

HRID 1790380Notes

Reaction equation

HRID 1790380 reaction equation
Br[CH2:2][CH2:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1.C[Mg]Br.[OH2:15].[C:16]([O:19][CH2:20]C)(=[O:18])C.[O:22]1[CH2:26]CCC1>C(OCC)C>[C:7]1([CH2:8][C:16]([O:19][CH3:20])=[O:18])[CH:10]=[CH:11][C:4]([CH2:3][C:2]([O:22][CH3:26])=[O:15])=[CH:5][CH:6]=1

Participants

7

Reactant 5

HCID 962WaterHCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 110851354-(2-Bromoethyl)benzaldehydeHCID 178418573HCID 178418573, compound

Product 1

HCID 5207741,4-Benzenediacetic acid, dimethyl esterYield 83.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

4-(2-Bromoethyl)benzaldehyde (3.245 g) was dissolved in tetrahydrofuran (60 ml). Under ice cooling, a 3 M solution (4.9 ml) of methylmagnesium bromide in diethyl ether was added dropwise thereinto and the resultant mixture was stirred for 1.5 hr. After adding water and ethyl acetate, the layers were separated and the organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was then purified by silica gel column chromatography (hexane/ethyl acetate system) to give the title compound (2.745 g) as a brown oil (yield: 83.8%).

Workup

  1. customthe layers were separated
  2. washthe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was then purified by silica gel column chromatography (hexane/ethyl acetate system)

Sources & evidence

ORD record
ord-37b599736875400c8225ce2333f92727
Source dataset
uspto-grants-2006_07
Patent number
US07071201B2

Reaction notes

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