Water → HCID 19004377, compound

HRID 2225849Notes

Reaction equation

HRID 2225849 reaction equation
C([O:3][C:4](=[O:26])[C:5](=[O:25])[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14](=[O:24])[C:15]2[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=2[CH3:23])=[CH:8][CH:7]=1)C.[OH-].[Na+].O>CO>[O:24]=[C:14]([C:15]1[C:16]([CH3:23])=[CH:17][C:18]([CH3:22])=[CH:19][C:20]=1[CH3:21])[CH2:13][O:12][C:9]1[CH:10]=[CH:11][C:6]([C:5](=[O:25])[C:4]([OH:26])=[O:3])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 67756697HCID 67756697, compound

Product 1

HCID 19004377HCID 19004377, compoundYield 73.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-[2-oxo-2-(2,4,6-trimethylphenyl]ethoxy]-alpha-oxobenzeneacetic acid ethyl ester (0.357 g) in hot methanol (5 mL) was treated with 1N sodium hydroxide (2 mL). Water (20 mL) was added, then after the methanol was removed in vacuo, the solution was acidified with 1N hydrochloric acid (2.5 mL) and extracted with dichloromethane methane (1×40 mL, 1×7 mL). The combined organic layers were washed with brine, then dried (MgSO4) and evaporated. The resulting residue was crystallized from diethyl ether-hexane to furnish 0.242 g of 4-[2-oxo-2-(2,4,6-trimethyl-phenyl]ethoxy]-alpha-oxobenzeneacetic acid, mp 144°-145° C.

Workup

  1. customafter the methanol was removed in vacuo
  2. extractionextracted with dichloromethane methane (1×40 mL, 1×7 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe resulting residue was crystallized from diethyl ether-hexane

Sources & evidence

ORD record
ord-675728515cff402da29860c6f0549a7b
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

Loading…