Trifluoroacetic anhydride → 6-methoxy-7-methyl-3,4-dihydronaphthalen-1(2H)-one

HRID 1859811Notes

Reaction equation

HRID 1859811 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:10][CH2:11][CH2:12][C:13]([OH:15])=O)[CH:6]=[CH:7][C:8]=1[CH3:9].FC(F)(F)C(OC(=O)C(F)(F)F)=O>C(Cl)Cl.CCOCC>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:6](=[CH:7][C:8]=1[CH3:9])[C:13](=[O:15])[CH2:12][CH2:11][CH2:10]2

Participants

5

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 186264724-(3-Methoxy-4-methylphenyl)butanoic acid

Product 1

HCID 113559636-methoxy-7-methyl-3,4-dihydronaphthalen-1(2H)-oneYield 54.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 5.6 g (26.9 mmol) of 4-(3-methoxy-4-methylphenyl)butanoic acid in 100 mL of CH2Cl2 was cooled in ice and treated dropwise with 25 mL of trifluoroacetic anhydride. After stirring at 0° C. for 1 hour, the solution was diluted with Et2O and washed twice with 5% NaOH, then with saturated NaCl. Drying over MgSO4 and removal of the solvent under reduced pressure left the crude product. Chromatography on silica gel, eluting with CH2Cl2 gave 2.79 g (54.7% yield) of the product as a white solid, mp 104-107° C. The structure was confirmed by NMR and mass spectroscopy. MS m/z 191 (M+H+).

Workup

  1. washwashed twice with 5% NaOH
  2. dry with materialDrying over MgSO4 and removal of the solvent under reduced pressure
  3. waitleft the crude product
  4. washChromatography on silica gel, eluting with CH2Cl2

Sources & evidence

ORD record
ord-845fbe76686048abbce0de3cb43ba391
Source dataset
uspto-grants-2003_03
Patent number
US06528535B2

Reaction notes

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