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

HRID 433675Notes

Reaction equation

HRID 433675 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 1 M 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 (233 mg, 91%). 1H NMR (400 MHz, CDCl3) δ 8.01-7.39 (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-f59f5c55b88045f184a5216a34d630e4
Source dataset
uspto-grants-2003_12
Patent number
US06667331B2

Reaction notes

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