Sodium Hydroxide → 5-(3-methoxyphenyl)pentanoic Acid

HRID 917484Notes

Reaction equation

HRID 917484 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15]CC)=[O:14])[CH:6]=[CH:7][CH:8]=1.[OH-].[Na+]>C1COCC1.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13816374Ethyl 5-(3-methoxyphenyl)pentanoate

Product 1

HCID 105844855-(3-methoxyphenyl)pentanoic AcidYield 85%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

A mixture of ethyl 5-(3-methoxyphenyl)pentanoate (1 equivalent) and sodium hydroxide (3 equivalents) in THF/H2O was heated at reflux overnight. THF was evaporated, the aqueous phase acidified with 6N HCl to pH<5, and then extracted with a mixture of chloroform:isopropyl alcohol (3:1, 5 times). The organic phase was dried over anhydrous sodium sulfate. A light yellow oil was obtained in more than 85% yield after removal of the solvent: 1H NMR δ 7.20 (m, 1H), 6.79-6.73 (m, 3H), 3.80 (s, 3H), 2.62 (m, 2H), 2.38 (m, 2H), 1.68 (m, 4H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. customTHF was evaporated
  4. extractionextracted with a mixture of chloroform:isopropyl alcohol (3:1, 5 times)
  5. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  6. customA light yellow oil was obtained in more than 85% yield
  7. customafter removal of the solvent

Sources & evidence

ORD record
ord-5b8102ccb4b84e35ab9a4a493325f3a7
Source dataset
uspto-grants-2007_09
Patent number
US07273880B2

Reaction notes

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