Sodium Hydroxide → 3-[4-(Phenoxymethyl)phenyl]propanoic acid

HRID 386430Notes

Reaction equation

HRID 386430 reaction equation
[O:1]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]([O:19]CC)=[O:18])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C1COCC1.CO>[O:1]([CH2:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67528977Ethyl 3-(4-(phenoxymethyl)phenyl)propanoate

Product 1

HCID 545821483-[4-(Phenoxymethyl)phenyl]propanoic acid

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

A solution of ethyl 3-(4-(phenoxymethyl)phenyl)propanoate (S26, 185 mg, 0.65 mmol) in a THF/MeOH (1/1, 10 mL) was treated with aqueous 4 N NaOH (1 mL) and was stirred overnight 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 S27 (115 mg, 0.45 mmol, 69%) as a pale yellow solid: 1H NMR (CDCl3, 500 MHz) 7.39 (d, 2H, J=7.7 Hz), 7.30 (t, 2H, J=7.4 Hz), 7.25 (d, 2H, J=7.7 Hz), 7.00-6.96 (m, 3H), 5.05 (s, 2H), 2.99 (t, 2H, J=7.7 Hz), 2.71 (t, 2H, J=7.7 Hz); 13C NMR (CDCl3, 125 MHz) 178.8, 158.7, 139.9, 135.1, 129.5, 128.5, 127.8, 120.9, 114.7, 69.7, 35.4, 30.2.

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 S27 (115 mg, 0.45 mmol, 69%) as a pale yellow solid

Sources & evidence

ORD record
ord-9f06cdab5f9c4526845316b4d479551a
Source dataset
uspto-grants-2013_02
Patent number
US08372823B2

Reaction notes

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