Chloroacetic Acid → HCID 54135854, compound

HRID 1194481Notes

Reaction equation

HRID 1194481 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:22]=[CH:21][C:8]2[C:9](=[O:20])[C:10]([C:13]3[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=3)=[CH:11][O:12][C:7]=2[C:6]=1[O:23][CH3:24].Cl[CH2:26][C:27]([OH:29])=[O:28]>CN(C)C=O>[CH3:3][O:4][C:5]1[CH:22]=[CH:21][C:8]2[C:9](=[O:20])[C:10]([C:13]3[CH:14]=[CH:15][C:16]([O:19][CH2:26][C:27]([OH:29])=[O:28])=[CH:17][CH:18]=3)=[CH:11][O:12][C:7]=2[C:6]=1[O:23][CH3:24]

Participants

5

Reactant 3

HCID 300Chloroacetic AcidHCID 24758Sodium hydrideHCID 21270158HCID 21270158, compound

Product 1

HCID 54135854HCID 54135854, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

NaH is dissolved in dry dimethylformamide under nitrogen atmosphere at 0°. 7,8-Dimethoxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one [cp. J. Inst. Chem. (Calcutta) 43, 234 (1971)], dissolved in dry dimethylformamide, is added slowly, then a solution of chloroacetic acid. The solution is heated at 70° for 5 h and evaporated under vacuum to about one third of its original volume. After cooling, water is added and a precipitate occurs which is filtered and crystallized in methanol to give 7,8-dimethoxy-3-(4-carboxymethoxyphenyl)-4H-1-benzopyran-4-one.

Workup

  1. additionis added slowly
  2. temperatureThe solution is heated at 70° for 5 h
  3. customevaporated under vacuum to about one third of its original volume
  4. temperatureAfter cooling
  5. additionwater is added
  6. filtrationis filtered
  7. customcrystallized in methanol

Sources & evidence

ORD record
ord-44f2459d10e948e7bb3201caa1ff2480
Source dataset
uspto-grants-1989_03
Patent number
US04814346

Reaction notes

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