Isobutyraldehyde → 2,2-Dimethyl-3-(3,5-dimethylphenyl)-propionaldehyde

HRID 985904

Reaction equation

HRID 985904 reaction equation
[OH-].[Na+].[CH3:3][C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([CH3:12])[CH:11]=1)[CH2:7]Cl.[CH:13](=[O:17])[CH:14]([CH3:16])[CH3:15]>[Br-].C([N+](C)(C)C)CCCCCCCCCCCCC.[I-].[K+].C1(C)C=CC=CC=1.O1CCCC1>[CH3:15][C:14]([CH3:16])([CH2:7][C:6]1[CH:5]=[C:4]([CH3:3])[CH:11]=[C:10]([CH3:12])[CH:9]=1)[CH:13]=[O:17]

Participants

8

Reactant 3

HCID 6561IsobutyraldehydeHCID 14798Sodium HydroxideHCID 1377003,5-Dimethylbenzyl chloride

Product 1

HCID 137973112,2-Dimethyl-3-(3,5-dimethylphenyl)-propionaldehydeYield 92%

Reagents, catalysts & solvents 4

HCID 4875Potassium IodideCatalystHCID 14250Tetradecyltrimethylammonium bromideCatalystHCID 1140TolueneSolvent2×HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
75 °C

Procedure

A pre-mix of 125 g of 30% by weight sodium hydroxide solution, 5 g of potassium iodide, 10 g of tetradecyltrimethylammonium bromide, 200 ml of tetrahydrofuran and 200 ml of toluene was heated to 75° C. A mixture of 155 g of 3,5-dimethylbenzyl chloride, 110 g of isobutyraldehyde, 50 ml of tetrahydrofuran and 50 ml of toluene was added dropwise to this pre-mix while stirring vigorously. The entire mixture was then boiled under reflux for 6 hours. The phases were then separated and the organic phase was first washed with warm water and then filtered with the addition of activated carbon. Finally, distillation was carried out using a packed column with wire spirals. The distillation, carried out in a temperature range of from 72° C. to 74° C. at 0.25 mbar, yielded 106 g of 92% 2,2-dimethyl-3-(3,5-dimethylphenyl)-propionaldehyde.

Workup

  1. additionwas added dropwise to
  2. additionthis pre-mix
  3. temperatureunder reflux for 6 hours
  4. customThe phases were then separated
  5. washthe organic phase was first washed with warm water
  6. filtrationfiltered with the addition of activated carbon
  7. distillationFinally, distillation
  8. distillationThe distillation
  9. customcarried out in a temperature range of from 72° C. to 74° C. at 0.25 mbar

Sources & evidence

ORD record
ord-f2ef4a85e9a04737bae7c8b6c5b234f1
Source dataset
uspto-grants-1987_12
Patent number
US04710316

Linked notes

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