Hydrochloric Acid → 2,2-Dimethyl-3-(2-naphthyl)propionic acid

HRID 2172716Notes

Reaction equation

HRID 2172716 reaction equation
[CH3:1][C:2]([CH3:19])([CH2:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=1)[C:3]([O:5]CC)=[O:4].Cl>O1CCOCC1.[OH-].[Na+].C(OCC)(=O)C>[CH3:1][C:2]([CH3:19])([CH2:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=1)[C:3]([OH:5])=[O:4]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 68378920Ethyl 2,2-dimethyl-3-(naphthalene-2-yl)propanoate

Product 1

HCID 98779422,2-Dimethyl-3-(2-naphthyl)propionic acidYield 40%

Reagents, catalysts & solvents 3

HCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

The crude ester (915 mg) was taken up in dioxane (4 mL) and 20% aqueous sodium hydroxide (8 mL). After stirring at room temperature for 2 hours, the reaction mixture was diluted with ethyl acetate. The aqueous fraction was acidified to pH=2 with concentrated hydrochloric acid and was then extracted with ethyl acetate. The combined organic fractions were dried over sodium sulfate and concentrated to yield 2,2-dimethyl-3-(naphthalene-2-yl)propanoic acid (211 mg, 40% yield for two steps) as a white solid, which was used directly in the next step.

Workup

  1. extractionwas then extracted with ethyl acetate
  2. dry with materialThe combined organic fractions were dried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-87bfc685320f4a5ebbc790c96a3ed436
Source dataset
uspto-grants-2015_06
Patent number
US09056852B2

Reaction notes

Loading…