Butyric Acid → 4-(3-Trifluoromethylphenyl)-7-methoxy-1-tetralone

HRID 2059317Notes

Reaction equation

HRID 2059317 reaction equation
FC(F)(F)C1C=C(C(C2C=CC(OC)=CC=2)CC(OCC)=O)C=CC=1.[F:26][C:27]([F:49])([F:48])[C:28]1[CH:29]=[C:30]([CH:34]([C:40]2[CH:45]=[CH:44][C:43]([O:46][CH3:47])=[CH:42][CH:41]=2)[CH2:35][CH2:36][C:37]([OH:39])=O)[CH:31]=[CH:32][CH:33]=1.C(#N)CCC.C(O)(=O)CCC.CS(O)(=O)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>C(O)CC>[F:49][C:27]([F:48])([F:26])[C:28]1[CH:29]=[C:30]([CH:34]2[C:40]3[C:41](=[CH:42][C:43]([O:46][CH3:47])=[CH:44][CH:45]=3)[C:37](=[O:39])[CH2:36][CH2:35]2)[CH:31]=[CH:32][CH:33]=1

Participants

8

Reactant 6

HCID 264Butyric AcidHCID 6395Methanesulfonic AcidHCID 8008ButyronitrileHCID 14812Phosphorus oxide (P4O10)HCID 16737857Ethyl 3-(3-trifluoromethylphenyl)-3-(4-methoxyphenyl)propionateHCID 541849194-(3-Trifluoromethylphenyl)-4-(4-methoxyphenyl) butanoic acid

Product 1

HCID 205459114-(3-Trifluoromethylphenyl)-7-methoxy-1-tetraloneYield 81%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

Ethyl 3-(3-trifluoromethylphenyl)-3-(4-methoxyphenyl)propionate was converted to 4-(3-trifluoromethylphenyl)-4-(4-methoxyphenyl) butanoic acid by standard methods, viz. reduction of the propionate ester to the propanol (93%) tosylation (81%), conversion to the butyronitrile (67%) and hydrolysis to the butanoic acid (85%), which was obtained as a pale yellow oil. This oil (10 g) was stirred overnight at room temperature in a solution of methanesulphonic acid (100 g) and phosphorus pentoxide (21 g). The mixture was poured onto ice, extracted with ether, the extracts washed with dilute sodium hydroxide, dried (MgSO4) and filtered through a short column of alumina. Removal of the ether gave 4-(3-trifluoromethylphenyl)-7-methoxy-1-tetralone as a pale yellow oil (7.65 g, 81%).

Workup

  1. customwhich was obtained as a pale yellow oil
  2. additionThe mixture was poured onto ice
  3. extractionextracted with ether
  4. washthe extracts washed with dilute sodium hydroxide
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered through a short column of alumina
  7. customRemoval of the ether

Sources & evidence

ORD record
ord-fc18eb758b874a9fb67c582032c62b39
Source dataset
uspto-grants-1982_03
Patent number
US04322370

Reaction notes

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