Hydrochloric Acid → Methyl methoxy-(4-methoxyphenyl)acetate

HRID 2235746Notes

Reaction equation

HRID 2235746 reaction equation
C[O-].[Na+].[C:4](O)(=[O:6])C.C(O)(=O)C.IC1C=CC=CC=1.[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][C:28]([O:30][CH3:31])=[O:29])=[CH:23][CH:22]=1.Cl>CO>[CH3:4][O:6][CH:27]([C:24]1[CH:23]=[CH:22][C:21]([O:20][CH3:19])=[CH:26][CH:25]=1)[C:28]([O:30][CH3:31])=[O:29]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 90266Methyl 4-methoxyphenylacetateHCID 10942334Sodium MethoxideHCID 12217721Iodo benzene diacetate

Product 1

HCID 10262525Methyl methoxy-(4-methoxyphenyl)acetateYield 15.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A 28% solution of sodium methoxide in methanol (12.8 g) and iodobenzene diacetate (7.15 g) were added to a solution of methyl 4-methoxyphenylacetate (4.0 g) in methanol (60 mL), and the reaction solution was stirred at room temperature for five days. 1 N hydrochloric acid (67 ml) was added dropwise to the reaction solution under ice-cooling, and methanol was evaporated from the reaction solution under reduced pressure. Ethyl acetate was added to the remaining aqueous layer, and the organic layer was separated. The resulting organic layer was sequentially washed with a saturated sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluting solvent: heptane-ethyl acetate system) to obtain 725 mg of the title compound. The property values of the compound are as follows.

Workup

  1. temperaturecooling
  2. custommethanol was evaporated from the reaction solution under reduced pressure
  3. additionEthyl acetate was added to the remaining aqueous layer
  4. customthe organic layer was separated
  5. washThe resulting organic layer was sequentially washed with a saturated sodium bicarbonate solution and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue was purified by silica gel column chromatography (eluting solvent: heptane-ethyl acetate system)

Sources & evidence

ORD record
ord-1a7016ceb45d4a0aa522173647f4f17d
Source dataset
uspto-grants-2010_05
Patent number
US07713993B2

Reaction notes

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