Hydrochloric Acid → 2-(4-(Naphthalen-2-yl)phenyl)acetic acid

HRID 433829Notes

Reaction equation

HRID 433829 reaction equation
[OH-].[Li+].O1CCCC1.C[O:9][C:10](=[O:28])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:27]=[CH:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=2)=[CH:14][CH:13]=1.Cl>CO>[CH:19]1[C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:26]=[CH:27][C:18]=1[C:15]1[CH:16]=[CH:17][C:12]([CH2:11][C:10]([OH:28])=[O:9])=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 20610300(4-Naphthalen-2-yl-phenyl)-acetic acid methyl ester

Product 1

HCID 113690362-(4-(Naphthalen-2-yl)phenyl)acetic acidYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Lithium hydroxide, 2M, (3.0 mL) was added to a 2:1 tetrahydrofuran:methanol (9.0 mL) solution of (4-Naphthalen-2-yl-phenyl)-acetic acid methyl ester (270 mg, 0.977 mmol). The resulting mixture was stirred at room temperature for 1 hour. The reaction was acidified to pH=1 with 1M hydrochloric acid and extracted twice with ethyl acetate. The combined organic portions were washed with brine, dried over magnesium sulfate and concentrated in vacuo to give the title compound as a white solid (233mg, 91%). 1H NMR (400 MHz, CDCl3) δ8.01-7.39 (m, 11H), 3.72 (s, 2H)

Workup

  1. extractionextracted twice with ethyl acetate
  2. washThe combined organic portions were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-03ee754ec5214d688ef78c65187d8634
Source dataset
uspto-grants-2003_12
Patent number
US06668527B2

Reaction notes

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