Sodium Carbonate → HCID 19004397, compound

HRID 2225820Notes

Reaction equation

HRID 2225820 reaction equation
C([O:3][C:4](=[O:31])[C:5](=[O:30])[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])[C:18]=2[CH2:27][CH2:28][CH3:29])=[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:30])[C:4]([OH:31])=[O:3])=[CH:7][CH:8]=2)=[C:18]([CH2:27][CH2:28][CH3:29])[C:19]=1[OH:26])(=[O:25])[CH3:24]

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 54143518HCID 54143518, compound

Product 1

HCID 19004397HCID 19004397, compoundYield 66.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 4-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-alpha-oxobenzeneacetic acid ethyl ester (0.7 g) in methanol (50 mL) was treated with sodium carbonate (0.38 g) in water (2.5 mL), and the reaction was stirred at room temperature for 2 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. The dried (Na2SO4) organic layer was evaporated, and the residue was crystallized from dichloromethane-hexane to yield in two crops, 0.435 g of 4-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-alpha-oxobenzeneacetic acid, mp 129°-130° C.

Workup

  1. customAfter the solvents were removed in vacuo, dichloromethane (40 mL) and water (40 mL)
  2. additionwere added
  3. dry with materialThe dried (Na2SO4) organic layer
  4. customwas evaporated
  5. customthe residue was crystallized from dichloromethane-hexane

Sources & evidence

ORD record
ord-a01ff1e319bb4f8c9ff298a67fd595e9
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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