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

HRID 14038Notes

Reaction equation

HRID 14038 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-5989021190884408ab74fb7b3edd02b5
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Reaction notes

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