Sodium Carbonate → HCID 19004390, compound

HRID 2225818Notes

Reaction equation

HRID 2225818 reaction equation
C([O:3][C:4](=[O:23])[C:5](=[O:22])[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)=[O:15])=[CH:8][CH:7]=1)C.C(=O)([O-])[O-].[Na+].[Na+]>CO.O>[N:16]1([C:14](=[O:15])[CH2:13][O:12][C:9]2[CH:8]=[CH:7][C:6]([C:5](=[O:22])[C:4]([OH:23])=[O:3])=[CH:11][CH:10]=2)[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 53914591HCID 53914591, compound

Product 1

HCID 19004390HCID 19004390, compoundYield 98.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

4-[2-(4-Morpholinyl)-2-oxoethoxy]-alpha-oxobenzeneacetic acid ethyl ester (0.4 g) in methanol (70 mL) was treated with sodium carbonate (0.158 g) in water (2 mL), and the mixture was stirred at room temperature for 1.5 hours. After the solvents were removed in vacuo, dichloromethane (40 mL) and water (40 mL) were added and the mixture was acidified with 3N hydrochloric acid. Tetrahydrofuran was added to dissolve the solids, then the separated aqueous layer was extracted twice with dichloromethane-tetrahydrofuran (1:1). The combined organic layers were dried (MgSO4), evaporated, and the residual solid was crystallized from dichloromethane-tetrahydrofuran-hexane to yield 0.36 g of 4-[2-(4-morpholinyl)-2-oxoethoxy]-alpha-oxobenzeneacetic acid, mp 182°-184° C.

Workup

  1. customAfter the solvents were removed in vacuo, dichloromethane (40 mL) and water (40 mL)
  2. additionwere added
  3. additionTetrahydrofuran was added
  4. dissolutionto dissolve the solids
  5. extractionthe separated aqueous layer was extracted twice with dichloromethane-tetrahydrofuran (1:1)
  6. dry with materialThe combined organic layers were dried (MgSO4)
  7. customevaporated
  8. customthe residual solid was crystallized from dichloromethane-tetrahydrofuran-hexane

Sources & evidence

ORD record
ord-eb43c2e6a45c4ecba30faa9f77a53d89
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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