Thionyl Chloride → HCID 20094804, compound

HRID 274072Notes

Reaction equation

HRID 274072 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH:10]([N+:16]([O-:18])=[O:17])[CH2:11][CH2:12][C:13]([OH:15])=O)[CH:6]=[CH:7][CH:8]=1.S(Cl)(Cl)=O.[Cl-].[Al+3].[Cl-].[Cl-]>ClCCCl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]2[C:13](=[O:15])[CH2:12][CH2:11][CH:10]([N+:16]([O-:18])=[O:17])[CH2:9][C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 6451240Aluminum(III) ChlorideHCID 200948615-(3-Methoxyphenyl)-4-nitrovaleric acid

Product 1

HCID 20094804HCID 20094804, compoundYield 83.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 5-(3-methoxyphenyl)-4-nitrovaleric acid (1.00 g) and thionyl chloride (0.34 ml) in 1,2-dichloroethane (2 ml) was refluxed for 1 hour. After cooling, aluminum chloride (0.53 g) was added to the solution at -12° C. and the whole was stirred for 0.5 hour. The solution was poured into ice water (15 ml). The organic layer was separated and the aqueous layer was extracted with dichloromethane. The combined organic layer was washed with an aqueous saturated sodium hydrogen carbonate solution, and brine, dried over anhydrous sodium sulfate, and evaporated in vacuo to give 2-methoxy-8-nitro-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-one (772 mg).

Workup

  1. temperaturewas refluxed for 1 hour
  2. temperatureAfter cooling
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with dichloromethane
  5. washThe combined organic layer was washed with an aqueous saturated sodium hydrogen carbonate solution, and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-4a7aff80bf914d55a42893f8af70bf79
Source dataset
uspto-grants-1995_02
Patent number
US05387710

Reaction notes

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