Hydrochloric Acid → (+)-4-(3'-Methylpentanoyl)biphenyl

HRID 26336

Reaction equation

HRID 26336 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.[Cl-].[Cl-].[Cl-].[Al+3].[CH3:17][CH:18]([CH2:23][CH3:24])[CH2:19][C:20](Cl)=[O:21].Cl>[N+](C1C=CC=CC=1)([O-])=O.O>[CH3:17][CH:18]([CH2:23][CH3:24])[CH2:19][C:20]([C:4]1[CH:5]=[CH:6][C:1]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[CH:2][CH:3]=1)=[O:21]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7095BiphenylHCID 6451240Aluminum(III) ChlorideHCID 126482793-Methylpentanoyl chloride

Product 1

HCID 21322796(+)-4-(3'-Methylpentanoyl)biphenyl

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7416NitrobenzeneSolvent

Conditions

Temperature
-7 °C

Procedure

To commercially available biphenyl (0.08 mole) and anhydrous aluminium trichloride (0.1 mole) dissolved in dry nitrobenzene (90ml), (+)-3-methylpentanoylchloride (0.1mole) the preparation of which is known and described in United Kingdom Patent Application No. 36211/75), is added in drops, the temperature being maintained at about -7° C. during the addition. The mixture is then stirred for about 18 hr. with cooling in an ice bath. It is then poured onto a mixture of ice, water and concentrated hydrochloric acid and stirred for 0.5 hr., and the nitrobenzene layer is separated. The nitrobenzene is removed by steam distillation and the residue is crystallised from a small volume of ethanol to constant melting point.

Workup

  1. addition36211/75), is added in drops
  2. temperaturewith cooling in an ice bath
  3. stirringstirred for 0.5 hr
  4. custom, and the nitrobenzene layer is separated
  5. customThe nitrobenzene is removed by steam distillation
  6. customthe residue is crystallised from a small volume of ethanol to constant melting point

Sources & evidence

ORD record
ord-d8bd9553888746338d44dceea6760389
Source dataset
uspto-grants-1979_04
Patent number
US04149413

Linked notes

Loading…