Benzene → HCID 54043382, compound

HRID 918013Notes

Reaction equation

HRID 918013 reaction equation
[CH2:1]=[CH:2][CH:3]=[CH2:4].[Cl:5]COC(C)C.[C:11](=[O:14])([O-])[O-].[Na+].[Na+].[CH:17]1[CH:22]=CC=C[CH:18]=1>[Cl-].[Zn+2].[Cl-]>[Cl:5][CH2:1][CH:2]=[CH:3][CH2:4][CH2:11][O:14][CH:17]([CH3:22])[CH3:18]

Participants

6

Reactant 4

HCID 241BenzeneHCID 78451,3-ButadieneHCID 10340Sodium CarbonateHCID 124317162-(Chloromethoxy)propane

Product 1

HCID 54043382HCID 54043382, compound

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

13 g (0.24 mol) of butadiene are introduced at 10°-15° during the course of 11/2 hours and while stirring into a suspension of 0.8 g of newly melted zinc chloride in 21.7 g (0.2 mol) of chloromethyl-isopropylether. The mixture which has now turned yellow is stirred at 10° for 1 hour. After this period 20 cc of 10% sodium carbonate solution are added dropwise, 100 cc of benzene are added and the aqueous phase is separated in a separatory funnel. The benzene solution is washed with 10% sodium carbonate solution and subsequently with water, is dried with magnesium sulphate and evaporated at reduced pressure. The residue is distilled at 90 mm. B.P. of 1-chloro-5-isopropoxy-2-pentene: 110°-112°/90 mm. nD20 = 1.4408.

Workup

  1. customthe aqueous phase is separated in a separatory funnel
  2. washThe benzene solution is washed with 10% sodium carbonate solution and subsequently with water
  3. dry with materialis dried with magnesium sulphate
  4. customevaporated at reduced pressure
  5. distillationThe residue is distilled at 90 mm
  6. custom110°-112°/90 mm

Sources & evidence

ORD record
ord-70a38cca58b34d40907b620c6bd1fcf2
Source dataset
uspto-grants-1976_07
Patent number
US03968235

Reaction notes

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