Sodium Carbonate → HCID 19004439, compound

HRID 2225836Notes

Reaction equation

HRID 2225836 reaction equation
C([O:3][C:4](=[O:28])[C:5](=[O:27])[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20]([C:23](=[O:25])[CH3:24])=[C:19]([OH:26])[CH:18]=2)=[CH:8][CH:7]=1)C.C(=O)([O-])[O-].[Na+].[Na+]>CO.O>[C:23]([C:20]1[CH:21]=[CH:22][C:17]([O:16][CH2:15][CH2:14][CH2:13][O:12][C:9]2[CH:10]=[CH:11][C:6]([C:5](=[O:27])[C:4]([OH:28])=[O:3])=[CH:7][CH:8]=2)=[CH:18][C:19]=1[OH:26])(=[O:25])[CH3:24]

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 54112140HCID 54112140, compound

Product 1

HCID 19004439HCID 19004439, compoundYield 89.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

As in example 10, 4-[3-(4-acetyl-3-hydroxyphenoxy)propoxy]-alpha-oxobenzeneacetic acid ethyl ester (0.7 g) in methanol (70 mL) was treated with a solution of sodium carbonate (0.42 g) in water and brought just to reflux temperature, then was allowed to cool to room temperature. After 1 hour, most of the methanol was removed in vacuo, then the mixture was diluted with water, acidified with 3N hydrochloric acid and extracted twice with dichloromethane-tetrahydrofuran (1:1). Evaporation of the dried (MgSO4) extracts and crystallization of the solid residue from dichlorornethane-hexane afforded 0.58 g of 4-[3-(4-acetyl-3-hydroxyphenoxy)propoxy]-alpha-oxobenzeneacetic acid, mp 133°-135° C.

Workup

  1. temperatureto reflux temperature
  2. custommost of the methanol was removed in vacuo
  3. additionthe mixture was diluted with water
  4. extractionextracted twice with dichloromethane-tetrahydrofuran (1:1)
  5. customEvaporation of the
  6. customdried
  7. custom(MgSO4) extracts and crystallization of the solid residue from dichlorornethane-hexane

Sources & evidence

ORD record
ord-ada977a90b43413eb7723315412655bc
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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