Dimethylformamide → Methyl 2-methoxybenzeneacetate

HRID 1600813Notes

Reaction equation

HRID 1600813 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-b376eb07279f4e209f17b7ef3b9a478a
Source dataset
uspto-grants-1999_11
Patent number
US05977118

Reaction notes

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