HCID 21275783, compound → Lilial

HRID 1382004Notes

Reaction equation

HRID 1382004 reaction equation
[Li]I.O.[CH:4]([C:6]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:15][CH:14]=1)(C)[C:7](OC)=O)=[O:5]>CN(P(N(C)C)(N(C)C)=O)C>[C:19]([C:16]1[CH:15]=[CH:14][C:13]([CH2:12][CH:6]([CH3:7])[CH:4]=[O:5])=[CH:18][CH:17]=1)([CH3:21])([CH3:20])[CH3:22]

Participants

4

Reactant 2

HCID 21275783HCID 21275783, compoundHCID 178526218HCID 178526218, compound

Product 1

HCID 228987LilialYield 105.1%

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent2×

Procedure

5 ml of hexamethylphosphortriamide (HMPT) and 1 g of LiI.H2O are heated to 240° C. under a nitrogen atmosphere. 1.1 g of crude methyl 2-formyl-2-p-tert.butyl-benzyl-propionate (82%) in 1 ml of HMPT are added thereto, the mixture is stirred for 1 minute, poured on to ice and extracted with hexane. After washing with 2N HCl, with sodium bicarbonate solution and water the organic phase is dried over magnesium sulphate and the solvent is evaporated. 0.9 g of crude p-tert.butyl-α-methyl-hydrocinnamaldehyde is obtained. After bulb-tube distillation 500 mg of this aldehyde give 300 mg of pure material. The yield therefore amounts to 78.8%.

Workup

  1. additionpoured on to ice
  2. extractionextracted with hexane
  3. washAfter washing with 2N HCl, with sodium bicarbonate solution and water the organic phase
  4. dry with materialis dried over magnesium sulphate
  5. customthe solvent is evaporated

Sources & evidence

ORD record
ord-b9853bafa562475b866246fe62c36e86
Source dataset
uspto-grants-1989_02
Patent number
US04804776

Reaction notes

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