4-Methoxy-3-methylbenzenebutanoic acid → 7-methoxy-6-methyl-3,4-dihydronaphthalen-1(2H)-one

HRID 1795586Notes

Reaction equation

HRID 1795586 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][C:12]([OH:14])=O)=[CH:5][C:4]=1[CH3:15].COC1C=CC(C(CC)C(O)=O)=CC=1C>CS(O)(=O)=O>[CH3:1][O:2][C:3]1[CH:8]=[C:7]2[C:6]([CH2:9][CH2:10][CH2:11][C:12]2=[O:14])=[CH:5][C:4]=1[CH3:15]

Participants

4

Reactant 2

HCID 8057164-Methoxy-3-methylbenzenebutanoic acidHCID 23221690HCID 23221690, compound

Product 1

HCID 102416217-methoxy-6-methyl-3,4-dihydronaphthalen-1(2H)-oneYield 88%

Reagents, catalysts & solvents 1

HCID 6395Methanesulfonic AcidSolvent

Procedure

A solution of 4-(4-methoxy-3-methylphenyl)butyric acid (Compound 27, 24.0 g, 115.4 mmol) and 400 mL of methanesulfonic acid was stirred at room temperature under the argon atmosphere for 24 h, then poured into ice, extracted three times with ethyl acetate, washed with NaHCO3 1 N, brine, dried over MgSO4, and filtered. The solvent was removed to give 19.2 g (88%) of the title compound as a dark brown solid.

Workup

  1. additionpoured into ice
  2. extractionextracted three times with ethyl acetate
  3. washwashed with NaHCO3 1 N, brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customThe solvent was removed

Sources & evidence

ORD record
ord-8cb513fbed904ae295598e4a1b3379c3
Source dataset
uspto-grants-2006_04
Patent number
US07026487B2

Reaction notes

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