Acetic Acid → HCID 5319678, compound

HRID 2228495Notes

Reaction equation

HRID 2228495 reaction equation
[N+](=C)=[N-].[CH3:4][O:5][C:6]1[C:7]([OH:17])=[C:8]([CH:12]=[CH:13][C:14]=1[O:15][CH3:16])[C:9]([OH:11])=[O:10].[C:18](O)(=O)C>C(OCC)C>[CH3:4][O:5][C:6]1[C:7]([OH:17])=[C:8]([CH:12]=[CH:13][C:14]=1[O:15][CH3:16])[C:9]([O:11][CH3:18])=[O:10]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 9550DiazomethaneHCID 797373,4-Dimethoxysalicylic acid

Product 1

HCID 5319678HCID 5319678, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of diazomethane in diethyl ether (30 ml, 0.25M, 0.0075 mol) was added to a solution of 3,4-dimethoxy-2-hydroxybenzoic acid (1.5 g, 0.0075 mol) in diethyl ether (50 ml) and the reaction stirred at room temperature for 10 minutes. Glacial acetic acid was then added and stirring continued for a further 18 hours. The reaction mixture was concentrated under reduced pressure and the residue partitioned between dichloromethane (40 ml) and aqueous sodium hydrogen carbonate solution (40 ml). The aqueous phase was further extracted with dichloromethane (100 ml), the combined organic extracts dried (MgSO4), filtered and evaporated under reduced pressure to give the subtitle compound as a white crystalline solid (1.5 g, 94%). 1H-NMR (CDCl3): Γ=3.82 (9H, m), 6.48 (1H, d), 7.58 (1H, d), 10.84 (1H, s).

Workup

  1. stirringstirring
  2. waitcontinued for a further 18 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe residue partitioned between dichloromethane (40 ml) and aqueous sodium hydrogen carbonate solution (40 ml)
  5. extractionThe aqueous phase was further extracted with dichloromethane (100 ml)
  6. dry with materialthe combined organic extracts dried (MgSO4)
  7. filtrationfiltered
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-12bdfafb8a7147ffb1c2eb026aac4e5b
Source dataset
uspto-grants-2002_07
Patent number
US06417194B1

Reaction notes

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