Methyl iodide → Methyl 2-(1,3-dioxaindan-5-yl)acetate

HRID 274926

Reaction equation

HRID 274926 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH2:10][C:11]([OH:13])=[O:12])=[CH:4][C:3]=2[O:2]1.[C:14](=O)([O-])[O-].[Cs+].[Cs+].CI>CN(C=O)C>[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:4][C:3]=2[O:2]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 76115Benzo-1,3-dioxole-5-acetic acid

Product 1

HCID 266588Methyl 2-(1,3-dioxaindan-5-yl)acetateYield 87.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of (3,4-methylenedioxyphenyl)acetic acid (4.64 g, 25.74 mmol) in dry DMF (40 mL), cesium carbonate (9.2 g, 25.74 mmol) and methyl iodide (3.7 g, 26.0 mmol) in dry DMF (40 mL) was stirred at room temperature for 3h. At the end of this period, the reaction mixture was poured into ice water and extracted with ethyl acetate. The organic phase was washed with saturated NaHCO3, water, brine and then dried (MgSO4) and filtered. The filtrate was concentrated in vacuo to provide pure methyl (3,4-methylenedioxyphenyl)acetate as an oil (4.38 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with saturated NaHCO3, water, brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-65362d73281c489fac77eb543a1e8af0
Source dataset
uspto-grants-1995_02
Patent number
US05391566

Linked notes

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