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

HRID 1166649Notes

Reaction equation

HRID 1166649 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]>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

3

Reactant 1

HCID 8057164-Methoxy-3-methylbenzenebutanoic acid2×

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 1N, 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 1N, brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customThe solvent was removed

Sources & evidence

ORD record
ord-9b8292d46a394d58a946db79ff069edf
Source dataset
uspto-grants-2003_09
Patent number
US06613917B1

Reaction notes

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