2-Propenal, 3-[4-(1,1-dimethylethyl)phenyl]-2-methyl- → Lilial

HRID 1903318

Reaction equation

HRID 1903318 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]=[C:12]([CH:14]=[O:15])[CH3:13])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[H][H]>O.[Pd]>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH2:11][CH:12]([CH3:13])[CH:14]=[O:15])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 1146592-Propenal, 3-[4-(1,1-dimethylethyl)phenyl]-2-methyl-HCID 178418361HCID 178418361, compound

Product 1

HCID 228987LilialYield 88.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

1420 g of 1-(p-tert.butylphenyl)-2-formyl-1-propene, prepared as described in paragraph (e), are mixed together with 6 g of 5% palladium/carbon and 6.8 g of soda in 20 ml of water at 70°-75° C. in a stirring autoclave. The autoclave is charged with hydrogen (8 atmospheres) and heated to 110° C. About 230 liters of hydrogen are absorbed after 12 hours. The crude 3-(p-tert.butyl-phenyl)-2-methyl-propionaldehyde is treated with ether, washed neutral with water and dried over sodium sulphate. After removing the ether, the product is fractionally distilled in vacuo. After separating a first running and a last running, there are obtained 1275 g of 3-(p-tert.butylphenyl)-2-methyl-propionaldehyde in 95% purity (about 88% of theory). Boiling point: 150°-152° C./15 mmHg; nD20 =1.5050.

Workup

  1. customAbout 230 liters of hydrogen are absorbed after 12 hours
  2. additionThe crude 3-(p-tert.butyl-phenyl)-2-methyl-propionaldehyde is treated with ether
  3. washwashed neutral with water
  4. dry with materialdried over sodium sulphate
  5. customAfter removing the ether
  6. distillationthe product is fractionally distilled in vacuo
  7. customAfter separating a first running

Sources & evidence

ORD record
ord-41740ed71faf4bc78ef173ba5d954b0f
Source dataset
uspto-grants-1984_03
Patent number
US04435585

Linked notes

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