4-Methyl-m-anisic acid → HCID 21956516, compound

HRID 2213089Notes

Reaction equation

HRID 2213089 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[CH3:12])[C:6]([OH:8])=O.[Li]C>C1COCC1.C(OCC)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[CH3:12])[C:6]([C:3]1[CH:4]=[CH:5][CH:9]=[CH:10][CH:11]=1)=[O:8]

Participants

5

Reactant 2

HCID 815794-Methyl-m-anisic acidHCID 178418348HCID 178418348, compound

Product 1

HCID 21956516HCID 21956516, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-methoxy-4-methyl benzoic acid (3.32 g, 20 mmol) in anhydrous THF (100 mL) was cooled to −78° C. A solution of MeLi (25 mL of a 1.6M solution in diethyl ether, 40 mmol) was added slowly to the reaction flask via syringe over 10 min. The cooling bath was removed, and the reaction mixture was allowed to warm to rt, and was stirred for 1 h at rt. The reaction mixture was quenched with 1N HCl (50 mL) and extracted with diethyl ether (3×50 mL). The organic extracts were combined, washed with brine (50 mL), dried (MgSO4), and concentrated to afford 3-methoxy-4-methyl benzophenone as a colorless oil.

Workup

  1. customThe cooling bath was removed
  2. customThe reaction mixture was quenched with 1N HCl (50 mL)
  3. extractionextracted with diethyl ether (3×50 mL)
  4. washwashed with brine (50 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-646fd6f2087c48b1bef375cdb2892c9c
Source dataset
uspto-grants-2006_09
Patent number
US07105533B2

Reaction notes

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