Tin tetrachloride → HCID 66650830, compound

HRID 417794Notes

Reaction equation

HRID 417794 reaction equation
[Sn](Cl)(Cl)(Cl)Cl.[C:6](Cl)(=[O:10])/[CH:7]=[CH:8]/[CH3:9].[CH2:12]([C:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH:17]=1)[CH:13]([CH3:15])[CH3:14]>ClCCl>[CH2:12]([C:16]1[CH:21]([C:6](=[O:10])/[CH:7]=[CH:8]/[CH3:9])[CH2:20][CH2:19][CH2:18][CH:17]=1)[CH:13]([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 24287Tin tetrachlorideHCID 138091Cyclohexene, 1-(2-methylpropyl)-HCID 643131trans-Crotonyl chloride

Product 1

HCID 66650830HCID 66650830, compoundYield 30.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

At −70° C., a solution of tin tetrachloride (533 ml, 4.54 mol, 1.4 eq.) in dichloromethane (2.5 l) was treated with crotonyl chloride (350 ml, 90%, 3.24 mol, 1.0 eq.). The resulting solution was stirred for 30 min. and treated within 1.5 h with a solution of 1-isobutylcyclohex-1-ene (448 g, 3.24 mol) in dichloromethane (400 ml). The resulting mixture was stirred for 1 h at −70° C. and poured into ice/H2O. The org. phase was first washed with concentrated NaOH then with H2O, dried (MgSO4), and the solvent evaporated. Short-path Vigreux-distillation (0.15 mbar, bath temperature: 160° C.) of the crude product (592 g) gave a fraction (495 g, boiling range: 90-130° C.) that was redistilled using again a short-path Vigreux-column (0.11 mbar, bath temperature: 160° C.) to give (E)-1-(2-isobutylcyclohex-2-enyl)but-2-en-1-one (202 g, 30%). Boiling point: 120° C. (0.11 mbar).

Workup

  1. stirringThe resulting mixture was stirred for 1 h at −70° C.
  2. washphase was first washed with concentrated NaOH
  3. dry with materialwith H2O, dried (MgSO4)
  4. customthe solvent evaporated
  5. distillationShort-path Vigreux-distillation (0.15 mbar, bath temperature: 160° C.) of the crude product (592 g)
  6. customgave a fraction (495 g, boiling range: 90-130° C.) that
  7. distillationwas redistilled
  8. customa short-path Vigreux-column (0.11 mbar, bath temperature: 160° C.)

Sources & evidence

ORD record
ord-4c0ca9fb90bc40959075b8f32c2d64c0
Source dataset
uspto-grants-2012_01
Patent number
US08093204B2

Reaction notes

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