Biphenyl → HCID 70574480, compound

HRID 1679911Notes

Reaction equation

HRID 1679911 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:13]12[C:19](=[O:20])[O:18][C:16](=[O:17])[CH:14]1[CH2:15]2.[Cl-].[Al+3].[Cl-].[Cl-]>C(=S)=S>[C:1]1([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:6]([C:19]([C@H:13]2[CH2:15][C@H:14]2[C:16]([OH:18])=[O:17])=[O:20])=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 7095BiphenylHCID 27347213-Oxabicyclo(3.1.0)hexane-2,4-dioneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 70574480HCID 70574480, compoundYield 31.4%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

12.7 g (82.4 millimoles) of biphenyl, followed by 10.0 g (89.2 millimoles) of 1,2-cyclopropanedicarboxylic acid anhydride, are added, in each case a little at a time, to 29.7 g (0.22 mole) of anhydrous aluminum chloride in 100 ml of carbon disulfide whilst stirring at room temperature. The mixture is refluxed for 4 hours and then left to stand for 2 days at ambient temperature. After decanting the carbon disulfide, the reaction mixture is introduced into 200 g of ice and 50 ml of concentrated hydrochloric acid. The solid which precipitates is filtered off, washed with water and recrystallized from propanol. 6.9 g (31% of theory) of cis-2-(p-biphenylcarbonyl)-cyclopropanecarboxylic acid are obtained as colorless crystals, of melting point 222°-223° C. after a further recrystallization, from ethanol.

Workup

  1. additionare added, in each case a little at a time
  2. temperatureThe mixture is refluxed for 4 hours
  3. waitleft
  4. customAfter decanting the carbon disulfide
  5. additionthe reaction mixture is introduced into 200 g of ice and 50 ml of concentrated hydrochloric acid
  6. customThe solid which precipitates
  7. filtrationis filtered off
  8. washwashed with water
  9. customrecrystallized from propanol

Sources & evidence

ORD record
ord-bb0107b1843541b59fbbec9e77e8a43d
Source dataset
uspto-grants-1981_06
Patent number
US04271163

Reaction notes

Loading…