Boron trifluoride etherate → 2-Methyl-3-[4-(2-methylbutan-2-yl)phenyl]propanal

HRID 1395216Notes

Reaction equation

HRID 1395216 reaction equation
C(O[C:5]([O:9]C(=O)C)(C)[CH:6]=[CH2:7])(=O)C.[C:13]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([CH2:16][CH3:17])([CH3:15])[CH3:14].B(F)(F)F.[CH3:28]COCC>[Ti](Cl)(Cl)(Cl)Cl.Cl>[C:13]([C:18]1[CH:19]=[CH:20][C:21]([CH2:28][CH:5]([CH3:9])[CH:6]=[O:7])=[CH:22][CH:23]=1)([CH2:16][CH3:17])([CH3:14])[CH3:15]

Participants

6

Reactant 3

HCID 8000Boron trifluoride etherateHCID 16295tert-Amylbenzene2×HCID 54435434alpha-Methyl-allylidene diacetate

Product 1

HCID 2289892-Methyl-3-[4-(2-methylbutan-2-yl)phenyl]propanal

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalyst2×HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 172 g of α-methyl-allylidene diacetate and 160 g of p-tert.amyl-benzene is allowed to drop in to a mixture, cooled to -10° C., of 637 g of p-tert.amyl-benzene, 211 g of titanium tetrachloride and 3 g of boron trifluoride etherate while stirring over a period of 1.5 hours. The mixture is subsequently stirred at -10° C. for 45 minutes and then poured on to a mixture of 800 ml of ice-water and 140 ml of concentrated hydrochloric acid in order to hydrolyse the titanium tetrachloride. The organic layer is separated, washed neutral with water and 5% sodium bicarbonate solution, dried over sodium sulphate and the excess p-tert.amyl-benzene is distilled in a water-jet vacuum. (Boiling point 108° C./20 Torr). The residue, crude 3-(p-tert.amyl-phenyl)-2-methyl-1-propenyl acetate, is taken up in 190 ml of methanol, treated with a solution of 80 g of potassium carbonate in 145 ml of water and heated at reflux with intensive stirring until the saponification has been completed. The methanol is distilled and the organic phase is separated and distilled. There is obtained pure 3-(p-tert.amyl-phenyl)-2-methyl-propionaldehyde of boiling point 109°-111° C./0.06 Torr.

Workup

  1. stirringThe mixture is subsequently stirred at -10° C. for 45 minutes
  2. customThe organic layer is separated
  3. washwashed neutral with water and 5% sodium bicarbonate solution
  4. dry with materialdried over sodium sulphate
  5. distillationthe excess p-tert.amyl-benzene is distilled in a water-jet vacuum
  6. additiontreated with a solution of 80 g of potassium carbonate in 145 ml of water
  7. temperatureheated
  8. temperatureat reflux
  9. stirringwith intensive stirring until the saponification
  10. distillationThe methanol is distilled
  11. customthe organic phase is separated
  12. distillationdistilled

Sources & evidence

ORD record
ord-ecd73df36e664584b40125c6e7d4b11d
Source dataset
uspto-grants-1980_05
Patent number
US04202894

Reaction notes

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