Ammonia → 4,4-Diphenyl-1-butene

HRID 2072220Notes

Reaction equation

HRID 2072220 reaction equation
N.[NH2-].[Na+].[C:4]1([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Br[CH2:18][CH:19]=[CH2:20].[Cl-].[NH4+]>O.C(OCC)C>[C:4]1([CH:10]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:20][CH:19]=[CH2:18])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

8

Reactant 5

HCID 222AmmoniaHCID 7580DiphenylmethaneHCID 7841Allyl bromideHCID 24533Sodium amideHCID 25517Ammonium Chloride

Product 1

HCID 118306504,4-Diphenyl-1-butene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 1.5 l. of liquid ammonia containing 19.5 g. of sodium amide was stirred while a solution of 84.1 g. of diphenylmethane dissolved in 200 ml. of diethyl ether was added dropwise over about thirty minutes. The reaction mixture was stirred for forty-five minutes after the addition was completed. A solution of 60.5 g. of 3-bromo-1-propene in 50 ml. of diethyl ether was then added to the reaction mixture, after which time the mixture was stirred for twelve hours. A saturated aqueous solution of ammonium chloride was then added to the reaction mixture, followed by the addition of 500 ml. of water. The product was extracted from the aqueous reaction mixture into diethyl ether. The ethereal extracts were combined, washed, and dried. Evaporation of the solvent under reduced pressure provided 93.2 g. of the product as an oil. Distillation of the crude oil afforded 4,4-diphenyl-1-butene, B.P. 95°-98° C. 0.10 torr.

Workup

  1. additionafter the addition
  2. stirringafter which time the mixture was stirred for twelve hours
  3. additionfollowed by the addition of 500 ml
  4. extractionThe product was extracted from the aqueous reaction mixture into diethyl ether
  5. washwashed
  6. customdried
  7. customEvaporation of the solvent under reduced pressure
  8. customprovided 93.2 g
  9. distillationDistillation of the crude oil

Sources & evidence

ORD record
ord-ac009650b2744e54b62ac252beb3ccd7
Source dataset
uspto-grants-1977_09
Patent number
US04049827

Reaction notes

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