Water → Benzenepropanal, alpha,alpha,3-trimethyl-

HRID 985901Notes

Reaction equation

HRID 985901 reaction equation
[OH-].[Na+].O.[CH3:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=1)[CH2:8]Cl.[CH:13](=[O:17])[CH:14]([CH3:16])[CH3:15]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1.C1(C)C=CC=CC=1>[CH3:15][C:14]([CH3:16])([CH2:8][C:7]1[CH:10]=[CH:11][CH:12]=[C:5]([CH3:4])[CH:6]=1)[CH:13]=[O:17]

Participants

8

Reactant 4

HCID 962WaterHCID 6561IsobutyraldehydeHCID 12102m-Xylyl chlorideHCID 14798Sodium Hydroxide

Product 1

HCID 13797308Benzenepropanal, alpha,alpha,3-trimethyl-

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A pre-mix of 23.3 g of NaOH, 2.5 g of tetrabutylammonium iodide, 107 ml of water, 25 ml of toluene and 9 ml of tetrahydrofuran under argon was heated to 70° C. A mixture of 70 g (0.5 moles) of 3-methylbenzyl chloride and 50.4 g (0.7 moles) of isobutyraldehyde was added dropwise to this pre-mix within a period of 2 hours while stirring vigorously. The reaction mixture was then maintained at a temperature of 75° C. for 3 hours. After separating the phases and removing the solvents, 66.5 g of end product were obtained by fractional distillation at 0.12 mbar in a temperature range of from 50° C. to 52° C.

Workup

  1. additionwas added dropwise to
  2. additionthis pre-mix within a period of 2 hours
  3. temperatureThe reaction mixture was then maintained at a temperature of 75° C. for 3 hours
  4. customAfter separating the phases
  5. customremoving the solvents, 66.5 g of end product
  6. customwere obtained by fractional distillation at 0.12 mbar in a temperature range of from 50° C. to 52° C.

Sources & evidence

ORD record
ord-fc35e75704424c6e9b73e486389cf5f4
Source dataset
uspto-grants-1987_12
Patent number
US04710316

Reaction notes

Loading…