Dimethylformamide → Methyl 2-methoxybenzeneacetate

HRID 2257042Notes

Reaction equation

HRID 2257042 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=O.[C:12]([O-])([O-])=O.[K+].[K+].CI.CN([CH:23]=[O:24])C>>[CH3:12][O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([O:24][CH3:23])=[O:11]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 11970(2-Hydroxyphenyl)acetic acid

Product 1

HCID 99590Methyl 2-methoxybenzeneacetateYield 92%

Procedure

To a solution of 2-hydroxyphenylacetic acid (25 g, 0.16 mol) in DMF (300 mL) was added K2CO3 (56.7 g, 0.41 mol), followed by methyl iodide (46.7 g, 0.32 mol). The reaction mixture was stirred for about 3 days, filtered and the filtrate was stripped. The residue was taken up in ethyl acetate, washed with water, saturated Na2CO3, then brine, and then the organic layer was dried over MgSO4, filtered and stripped to afford 26.4 g (92%) of methyl 2-methoxyphenylacetate.

Workup

  1. filtrationfiltered
  2. washwashed with water, saturated Na2CO3
  3. dry with materialbrine, and then the organic layer was dried over MgSO4
  4. filtrationfiltered

Sources & evidence

ORD record
ord-228fae9f0c4a41a28ebccdc572d6d44f
Source dataset
uspto-grants-1997_08
Patent number
US05656629

Reaction notes

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