Water → methyl 2-(4-formyl-2-methoxyphenoxy)acetate

HRID 428690Notes

Reaction equation

HRID 428690 reaction equation
[O:1]=[CH:2][C:3]1[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=1.[H-].[Na+].Br[CH2:15][C:16]([O:18][CH3:19])=[O:17].O>C1COCC1.CN(C=O)C>[CH3:19][O:18][C:16](=[O:17])[CH2:15][O:9][C:8]1[CH:10]=[CH:11][C:3]([CH:2]=[O:1])=[CH:4][C:5]=1[O:6][CH3:7]

Participants

7

Reactant 4

HCID 962WaterHCID 1183VanillinHCID 24758Sodium hydrideHCID 60984Methyl bromoacetate

Product 1

HCID 882523methyl 2-(4-formyl-2-methoxyphenoxy)acetate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

(4-Formyl-2-methoxy-phenoxy)-acetic acid methyl ester was prepared by dissolving vanillin (4.1 mmol) (Aldrich) in dry THF (10 mL) and dry DMF (1 mL). Sodium hydride (109 mg, 4.5 mmol) was then added to the solution slowly and the resulting mixture was stirred at room temperature for 1 h at which time methyl bromoacetate (5 mmol) (Aldrich) was added dropwise. The reaction was stirred at room temperature for 14 h at which time water (10 mL) was added and the THF was evaporated in vacuo. The aqueous layer was then extracted with ethyl acetate (3×15 mL), and the combined organic layers were dried over magnesium sulfate and concentrated. The resulting (4-formyl-2-methoxy-phenoxy)-acetic acid methyl ester was purified via flash column chromatography (SiO2, 230-400 mesh) with ethyl acetate/hexane.

Workup

  1. additionwas added dropwise
  2. additionwas added
  3. customthe THF was evaporated in vacuo
  4. extractionThe aqueous layer was then extracted with ethyl acetate (3×15 mL)
  5. dry with materialthe combined organic layers were dried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe resulting (4-formyl-2-methoxy-phenoxy)-acetic acid methyl ester was purified via flash column chromatography (SiO2, 230-400 mesh) with ethyl acetate/hexane

Sources & evidence

ORD record
ord-8fc41e6e08454fd492f079c5ed36feff
Source dataset
uspto-grants-2001_11
Patent number
US06313310B1

Reaction notes

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