4-Oxo-undecanoyl Chloride → HCID 54155424, compound

HRID 1018162Notes

Reaction equation

HRID 1018162 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([CH3:18])=[CH:13][O:14][C:15](=[O:17])[CH3:16])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CC(C)([O-])C.[K+].[O:25]=[C:26]([CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[CH2:27]CC(Cl)=O>O1CCCC1>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH2:11][C:12]([CH3:18])=[CH:13][O:14][C:15](=[O:17])[CH2:16][CH2:27][C:26](=[O:25])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 229905004-Oxo-undecanoyl ChlorideHCID 23665647Potassium tert-butoxideHCID 53757095Acetic Acid 3-(4-tert-butyl-phenyl)-2-methyl-propenyl Ester

Product 1

HCID 54155424HCID 54155424, compoundYield 37.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of 43.79 g acetic acid 3-(4-tert-butyl-phenyl)-2-methyl-propenyl ester in 200 ml of tetrahydrofuran, a solution of 27.16 g potassium tert-butoxide in 200 ml of tetrahydrofuran was added at −78° C. After stirring at this temperature for 90 minutes, a solution of 53.00 g 4-oxo-undecanoyl chloride in 200 ml of tetrahydrofuran was added. After stirring at −78° C. for 2.5 hours, the solution was quenched with saturated sodium bicarbonate solution and diluted with ether. The organic phase was washed with saturated sodium bicarbonate solution and brine, dried and evaporated to dryness. The residue was purified by thin-film distillation and chromatography to yield 25.73 g of a yellow oil.

Workup

  1. stirringAfter stirring at −78° C. for 2.5 hours
  2. customthe solution was quenched with saturated sodium bicarbonate solution
  3. additiondiluted with ether
  4. washThe organic phase was washed with saturated sodium bicarbonate solution and brine
  5. customdried
  6. customevaporated to dryness
  7. distillationThe residue was purified by thin-film distillation and chromatography

Sources & evidence

ORD record
ord-d8bd35504fa242419eac4313dd5bf1f6
Source dataset
uspto-grants-2002_11
Patent number
US06479682B1

Reaction notes

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