Sodium Hydroxide → HCID 62738841, compound

HRID 2172713Notes

Reaction equation

HRID 2172713 reaction equation
C([O:3][C:4](=[O:17])[C:5]([CH3:16])([CH3:15])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH3:14])[CH:8]=1)C.[OH-].[Na+]>C(O)C>[CH3:14][O:13][C:9]1[CH:8]=[C:7]([CH2:6][C:5]([CH3:16])([CH3:15])[C:4]([OH:17])=[O:3])[CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68379075HCID 68379075, compound

Product 1

HCID 62738841HCID 62738841, compoundYield 68.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The crude ethyl-3-(3-methoxyphenyl)-2,2-dimethylpropanoate (1.00 g, 4.23 mmol) was taken up in a solution of ethanol (50 mL) and sodium hydroxide (2 N, 10 mL). The reaction mixture was refluxed overnight and then concentrated under vacuum. The concentrated aqueous solution was acidified with hydrochloric acid (2 N) to pH 3-4 and extracted with ethyl acetate. The combined organic fractions were dried over sodium sulfate and evaporated to yield 3-(3-methoxyphenyl)-2,2-dimethylpropanoic acid (600 mg) as a brown oil, which was used directly in the next step. MS m/z: 207 (M−1).

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. concentrationconcentrated under vacuum
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic fractions were dried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-200c9074efbf4c5fa5dba3d9c1f4b9cc
Source dataset
uspto-grants-2015_06
Patent number
US09056852B2

Reaction notes

Loading…