HCID 21086190, compound → 3-Methyl-5-pentanoylbenzoic acid

HRID 348832Notes

Reaction equation

HRID 348832 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([C:12](=[O:17])[CH2:13][CH2:14][CH2:15][CH3:16])[CH:11]=1)[C:5]([O:7]C)=[O:6].C1COCC1.CO.[OH-].[Na+]>CO.C(OCC)(=O)C>[CH3:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([C:12](=[O:17])[CH2:13][CH2:14][CH2:15][CH3:16])[CH:11]=1)[C:5]([OH:7])=[O:6]

Participants

5

Reactant 2

HCID 21086190HCID 21086190, compoundHCID 68905432THF methanol sodium hydroxide

Product 1

HCID 210858393-Methyl-5-pentanoylbenzoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of methyl 3-methyl-5-pentanoylbenzoate (LXXVI, step 2. 133 mg, 0.605 mmol) in methanol (1 mL) is stirred with tetrahydrofuran/methanol/sodium hydroxide (2 N) (3/1/1, 3 mL) for 3 days. The reaction mixture is diluted with ethyl acetate and washed with water. The aqueous phase is separated and acidified with hydrochloric acid (1 N) and extracted with methylene chloride. The organic phase is dried (sodium sulfate), filtered, and concentrated under reduced pressure to give 3-methyl-5-pentanoylbenzoic acid (IX–LXXVII), NMR (300 MHz, CD3OD): δ 8.44, 8.03, 3.10, 2.33, 1.78, 1.64 and 1.34.

Workup

  1. washwashed with water
  2. customThe aqueous phase is separated
  3. extractionextracted with methylene chloride
  4. dry with materialThe organic phase is dried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-678c50b1a055439b8839df3951cf0ab8
Source dataset
uspto-grants-2007_02
Patent number
US07176242B2

Reaction notes

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