Citric Acid → HCID 23111674, compound

HRID 1163314Notes

Reaction equation

HRID 1163314 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:29]=[CH:30][CH:31]=1)[CH2:11][O:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[CH:19]([CH2:23][C:24]([O:26]CC)=[O:25])[CH2:18][CH2:17][CH2:16]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)C.[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O.O1CCCC1>[O:1]([C:8]1[CH:9]=[C:10]([CH:29]=[CH:30][CH:31]=1)[CH2:11][O:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[CH:19]([CH2:23][C:24]([OH:26])=[O:25])[CH2:18][CH2:17][CH2:16]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 311Citric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 58755280HCID 58755280, compound

Product 1

HCID 23111674HCID 23111674, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl (6-((3-phenoxybenzyl)oxy)-1,2,3,4-tetrahydro-1-naphthalenyl)acetate (0.481 g, 1.15 mmol) in a mixed solvent of ethanol (4 mL) and tetrahydrofuran (4 mL) was added 2 M aqueous sodium hydroxide solution (2 mL), and the mixture was stirred at room temperature for 9 hr. Water was added to the reaction mixture, and the mixture was neutralized with 10% aqueous citric acid solution and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate-hexane to give the title compound (0.360 g, yield 81%) as colorless needle crystals.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-a0a7f341507e498aa745ddecabb02be3
Source dataset
uspto-grants-2010_10
Patent number
US07820837B2

Reaction notes

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