Hydrochloric Acid → 4-(3-Chloro-1-phenyl-1-propenyl)(1,1'-biphenyl)

HRID 2305260

Reaction equation

HRID 2305260 reaction equation
[C:1]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:6]=[CH:5][C:4]([C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=O)=[CH:3][CH:2]=1.[CH:21]([Mg]Cl)=[CH2:22].[ClH:25]>C1COCC1>[Cl:25][CH2:21][CH:22]=[C:7]([C:4]1[CH:5]=[CH:6][C:1]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:2][CH:3]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 750404-BenzoylbiphenylHCID 178461836HCID 178461836, compound

Product 1

HCID 570094044-(3-Chloro-1-phenyl-1-propenyl)(1,1'-biphenyl)Yield 29%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ((1,1′-biphenyl)-4-yl)phenylmethanone (0.01 mol) in THF (200 ml) was stirred at room temperature under N2 flow. Vinylmagnesium chloride (0.011 mol; 1M solution in THF) was added dropwise. The mixture was stirred at room temperature for 1 hour. HCl (150 ml) was added. The mixture was stirred at room temperature for 1 hour and extracted with DIPE. The organic layer was separated, washed once with a saturated K2CO3 solution, twice with H2O and once with a saturated NaCl solution, then dried, filtered and the solvent was evaporated. This fraction was purified by column chromatography over silica gel (eluent: CH2Cl2hexane/EtOAc 50/30/20). Two pure fractions were collected and their solvents were evaporated, yielding 8.8 g (29%) of 4-(3-chloro-1-phenyl-1-propenyl)(1,1′-biphenyl) (interm. 22).

Workup

  1. stirringThe mixture was stirred at room temperature for 1 hour
  2. stirringThe mixture was stirred at room temperature for 1 hour
  3. extractionextracted with DIPE
  4. customThe organic layer was separated
  5. washwashed once with a saturated K2CO3 solution, twice with H2O and once with a saturated NaCl solution
  6. customdried
  7. filtrationfiltered
  8. customthe solvent was evaporated
  9. customThis fraction was purified by column chromatography over silica gel (eluent: CH2Cl2hexane/EtOAc 50/30/20)
  10. customTwo pure fractions were collected
  11. customtheir solvents were evaporated

Sources & evidence

ORD record
ord-1e54e7dcf6924754bac88b282dec0285
Source dataset
uspto-grants-2002_08
Patent number
US06440440B1

Linked notes

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