Water → Lilial

HRID 2051743Notes

Reaction equation

HRID 2051743 reaction equation
[C:1]([C:5]1[CH:16]=[CH:15][C:8]([C:9](Cl)=[C:10]([CH3:13])[CH:11]=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].O.[H][H]>[Pd].CO>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][CH:10]([CH3:13])[CH:11]=[O:12])=[CH:15][CH:16]=1)([CH3:3])([CH3:2])[CH3:4]

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 54149657HCID 54149657, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 228987LilialYield 88%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

4-tert-Butyl-β-chloro-α-methylcinnamaldehyde (71 g), 1.0 g of 5% Pd/C, 40 g of 30% sodium hydroxide solution, 40 g of water and 32 g of methanol were placed in a Parr apparatus and hydrogenated at 20-50 psi until the theoretical amount of hydrogen had been absorbed (about 31/2 hrs.). The solution was filtered and the aqueous phase extracted with 100 g of ethylene dichloride. The solution was distilled to yield 53.9 g (76%) of the desired product, bp 100° (1.0 mm).

Workup

  1. customhad been absorbed (about 31/2 hrs.)
  2. filtrationThe solution was filtered
  3. extractionthe aqueous phase extracted with 100 g of ethylene dichloride
  4. distillationThe solution was distilled

Sources & evidence

ORD record
ord-6779358edc5940ebb0a9575c142c05eb
Source dataset
uspto-grants-1980_01
Patent number
US04182730

Reaction notes

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