Dimethylformamide → HCID 58858094, compound

HRID 1916359Notes

Reaction equation

HRID 1916359 reaction equation
[K].[N+:2]([C:5]1[CH:6]=[C:7]([OH:13])[C:8]([O:11][CH3:12])=[CH:9][CH:10]=1)([O-:4])=[O:3].Cl[CH2:15][C:16](=[O:18])C.[CH3:19]N(C=O)C>O>[CH3:19][O:13][C:7]1[CH:6]=[C:5]([N+:2]([O-:4])=[O:3])[CH:10]=[CH:9][C:8]=1[O:11][CH2:12][C:16](=[O:18])[CH3:15]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6571ChloroacetoneHCID 694712-Methoxy-5-nitrophenolHCID 5462222Potassium

Product 1

HCID 58858094HCID 58858094, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of the potassium salt of 4-nitroguaiacol (2.00 g, 9.65 mmol) and chloroacetone (1.15 mL, 14.5 mmol) in 20 mL of DMF was heated at 80° C. for 3 h. The suspension was cooled to rt and diluted with water. A precipitate formed which was filtered, washed with water and dried under vacuum to afford the title compound (1.63 g) as an off-white solid. 1H NMR (CDCl3) δ 2.29 (s, 3H), 3.96 (s, 3H), 4.71 (s, 2H), 6.74 (d, J=8.80 Hz, 1H), 7.76 (d, J=2.20 Hz, 1H), 7.84 (dd, J=8.79 Hz, 2.20 Hz, 1H); 13C NMR (CDCl3) δ 26.37, 56.33, 73.62, 107.11, 111.88, 117.36, 142.33, 149.23, 152.49, 203.40; HPLC (Method #1): 1.98 min, (100%); LCMS (ES): m/z 226 [M+H]+.

Workup

  1. temperatureThe suspension was cooled to rt
  2. customA precipitate formed which
  3. filtrationwas filtered
  4. washwashed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-1dc656e55a2349709b32ffb60f3d2529
Source dataset
uspto-grants-2013_12
Patent number
US08618115B2

Reaction notes

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