Dimethylformamide → HCID 596473, compound

HRID 722793Notes

Reaction equation

HRID 722793 reaction equation
[C:1]([CH2:4][C:5]1[CH:13]=[CH:12][CH:11]=[C:10]([OH:14])[C:6]=1C(O)=O)([OH:3])=[O:2].[C:15]([O-:18])([O-])=O.[K+].[K+].[CH3:21]I.CN([CH:26]=[O:27])C>>[CH3:15][O:18][C:26](=[O:27])[C:6]1[C:5]([CH2:4][C:1]([O:3][CH3:21])=[O:2])=[CH:13][CH:12]=[CH:11][C:10]=1[OH:14]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 127516562-(Carboxymethyl)-6-hydroxybenzoic acid

Product 1

HCID 596473HCID 596473, compoundYield 56%

Conditions

Temperature
0 °C

Procedure

To a solution of 2-Carboxymethyl-6-hydroxy-benzoic acid (5.021 g, 25.6 mmol) in DMF (100 mL) at 0° C. were added K2CO3 (3.567 g, 25.9 mmol) and CH3I (7.9 mL, 51.9 mmol). After stirring under nitrogen at 0° C. for 4 h, the reaction was partitioned between H2O (100 mL) and ether (150 mL). The aqueous layer was acidified with 1 N HCl and extracted with EtOAc (200 mL). The EtOAc layer was dried over MgSO4 and concentrated in vacuo to give the crude 2-hydroxy-6-methoxycarbonylmethyl-benzoic acid methyl ester as a colorless oil (3.2 g, 56%): 1H NMR (CDCl3) δ 3.69 (s, 3H), 3.89 (s, 5H), 6.72 (d, J=6.7 Hz, 1H), 6.96 (d, J=8.0 Hz, 1H), 7.33–7.38 (m, 1H).

Workup

  1. customthe reaction was partitioned between H2O (100 mL) and ether (150 mL)
  2. extractionextracted with EtOAc (200 mL)
  3. dry with materialThe EtOAc layer was dried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f663ffe0c98f41a5a999198f7343340a
Source dataset
uspto-grants-2006_11
Patent number
US07138543B2

Reaction notes

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