Hydrochloric Acid → HCID 23111658, compound

HRID 1163312Notes

Reaction equation

HRID 1163312 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)[C:19]([CH2:23][C:24]([O:26]CC)=[O:25])=[CH: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+].Cl>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)[C:19]([CH2:23][C:24]([OH:26])=[O:25])=[CH: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 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 58755276HCID 58755276, compound

Product 1

HCID 23111658HCID 23111658, compoundYield 34.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of ethyl {6-[(3-phenoxybenzyl)oxy]-3,4-dihydronaphthalen-1-yl}acetate (0.622 g, 1.50 mmol) in a mixed solvent of ethanol (3 mL) and tetrahydrofuran (3 mL) was added 2 M aqueous sodium hydroxide solution (3 mL), and the mixture was stirred at room temperature for 1 hr and further at 70° C. for 5 hr. Water was added to the reaction mixture, and the mixture was acidified with 1 M hydrochloric acid 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 purified by silica gel column chromatography (20%-80% ethyl acetate/hexane) and recrystallized from ethyl acetate-hexane to give the title compound (0.198 g, yield 34%) 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 purified by silica gel column chromatography (20%-80% ethyl acetate/hexane)
  6. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-c868ab52ee204cdeaa582596a956e7ed
Source dataset
uspto-grants-2010_10
Patent number
US07820837B2

Reaction notes

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