Thionyl Chloride → HCID 13300848, compound

HRID 463510Notes

Reaction equation

HRID 463510 reaction equation
[F:1][C:2]([F:29])([F:28])[C:3]1[CH:27]=[CH:26][C:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]([CH:14]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:15][C:16](O)=[O:17])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.S(Cl)(Cl)=O>C1C=CC=CC=1>[F:29][C:2]([F:28])([F:1])[C:3]1[CH:27]=[CH:26][C:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]([CH:14]3[CH2:19][C:20]4[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=4)[C:16](=[O:17])[CH2:15]3)=[CH:10][CH:9]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 13300847HCID 13300847, compound

Product 1

HCID 13300848HCID 13300848, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

3-(4(p-trifluoromethylphenoxy)phenyl)-4-phenylbutyric acid (23 g) was refluxed in benzene with thionyl chloride (46 ml) for one hour. The solution was then evaporated to dryness and the residue dissolved in benzene (23 ml). A solution of stannic chloride (23 g) in benzene (46 ml) was added at 0° with stirring. The solution was allowed to stir at 0° for 0.5 hr. Ice; water, diethylether and dilute HCl were then added sequentially. The ether extracts were further washed with aqueous potassium hydroxide and evaporated to give 3-(4-(p-trifluoromethylphenoxy)phenyl)tetralone m.p. 136°-137° (ethanol).

Workup

  1. customThe solution was then evaporated to dryness
  2. dissolutionthe residue dissolved in benzene (23 ml)
  3. additionA solution of stannic chloride (23 g) in benzene (46 ml) was added at 0°
  4. stirringto stir at 0° for 0.5 hr
  5. additionwater, diethylether and dilute HCl were then added sequentially
  6. washThe ether extracts were further washed with aqueous potassium hydroxide
  7. customevaporated

Sources & evidence

ORD record
ord-ddca9abd250f4496b7dfd262b8fdeefe
Source dataset
uspto-grants-1985_05
Patent number
US04520007

Reaction notes

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