Sodium Hydroxide → 3-(4-Benzylphenyl)propanoic acid

HRID 386439Notes

Reaction equation

HRID 386439 reaction equation
[CH2:1]([C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][C:16]([O:18]CC)=[O:17])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C1COCC1.CO>[CH2:1]([C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67528821HCID 67528821, compound

Product 1

HCID 206529113-(4-Benzylphenyl)propanoic acid

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

A solution of ethyl 3-(4-benzylphenyl)propanoate (S39, 320 mg, 1.19 mmol) in THF/MeOH (1/1, 10 mL) was treated with aqueous 4 N NaOH (1 mL) and stirred for 3 h at 25° C. The reaction mixture was concentrated, diluted with aqueous 1 N HCl and extracted with CH2Cl2. The organic layer was dried over Na2SO4, filtered and concentrated to afford S40 (260 mg, 1.08 mmol, 91%) as a white solid: 1H NMR (CDCl3, 500 MHz) 7.27-7.06 (m, 9H), 3.91 (s, 2H), 2.86 (br s, 2H), 2.59 (br s, 2H); 13C NMR (CDCl3, 100 MHz) 179.9, 141.1, 138.8, 138.4, 128.9, 128.8, 128.4, 128.2, 126.0, 41.4, 36.9, 30.7.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with aqueous 1 N HCl
  3. extractionextracted with CH2Cl2
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto afford S40 (260 mg, 1.08 mmol, 91%) as a white solid

Sources & evidence

ORD record
ord-27c274f823ad4c53a6403a8609bd6709
Source dataset
uspto-grants-2013_02
Patent number
US08372823B2

Reaction notes

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