Hydrochloric Acid → HCID 23111704, compound

HRID 1163316Notes

Reaction equation

HRID 1163316 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][O:16][C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[CH:23]([CH2:27][C:28]([O:30]CC)=[O:29])[CH2:22][CH2:21][CH2:20]3)[CH:10]=1.C(O)C.[OH-].[Na+].Cl>O.O1CCCC1>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][O:16][C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[CH:23]([CH2:27][C:28]([OH:30])=[O:29])[CH2:22][CH2:21][CH2:20]3)[CH:10]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 58755285HCID 58755285, compound

Product 1

HCID 23111704HCID 23111704, compoundYield 57.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl (6-[(2′,6′-dimethylbiphenyl-3-yl)methoxy]-1,2,3,4-tetrahydronaphthalen-1-yl)acetate (0.15 g, 0.35 mmol) in a mixed solvent of ethanol (1 mL) and tetrahydrofuran (1 mL) was added 2 M aqueous sodium hydroxide solution (0.5 mL), and the mixture was stirred at room temperature for 18 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 recrystallized from ethyl acetate-hexane to give the title compound (0.08 g, yield 57%) as colorless prism 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-c0dfe618ffeb447b930f8d04d7dc2bf0
Source dataset
uspto-grants-2010_10
Patent number
US07820837B2

Reaction notes

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