Hydrochloric Acid → 2-[(E)-3,7-dimethyl-octa-2,6-dienyloxy]-1-(4-hydroxy-3,5-di-isopropyl-phenyl)-ethanone

HRID 1163467Notes

Reaction equation

HRID 1163467 reaction equation
[CH3:1]/[C:2](/[CH2:6][CH2:7][CH:8]=[C:9]([CH3:11])[CH3:10])=[CH:3]\[CH2:4][OH:5].[OH-].[K+].Cl[CH2:15][C:16]([C:18]1[CH:23]=[C:22]([CH:24]([CH3:26])[CH3:25])[C:21]([OH:27])=[C:20]([CH:28]([CH3:30])[CH3:29])[CH:19]=1)=[O:17].Cl>CN1CCCC1=O>[CH3:1]/[C:2](/[CH2:6][CH2:7][CH:8]=[C:9]([CH3:11])[CH3:10])=[CH:3]\[CH2:4][O:5][CH2:15][C:16]([C:18]1[CH:19]=[C:20]([CH:28]([CH3:30])[CH3:29])[C:21]([OH:27])=[C:22]([CH:24]([CH3:26])[CH3:25])[CH:23]=1)=[O:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 637566GeraniolHCID 858900592-Chloro-1-(4-hydroxy-3,5-di-isopropylphenyl)-ethanone

Product 1

HCID 577472402-[(E)-3,7-dimethyl-octa-2,6-dienyloxy]-1-(4-hydroxy-3,5-di-isopropyl-phenyl)-ethanoneYield 52.9%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent2×

Procedure

To a solution of 86.4 g (560 mmol) of (E)-3,7-dimethyl-octa-2,6-dien-1-ol and 64.5 g (1150 mmol) of potassium hydroxide in 150 ml of N-methylpyrrolidone a solution of 58.59 g (230 mmol) of 2-chloro-1-(4-hydroxy-3,5-di-iso-propylphenyl)-ethanone in 100 ml of N-methylpyrrolidone is added dropwise at room temperature and under inert atmosphere. After the addition is completed stirring is continued for additional 16 hours. Then the reaction mixture is acidified with 1N HCl and extracted with ethyl acetate. The collected organic phases are washed with water and brine, dried and evaporated. Crystallization of the crude product from hexane gives 45.3 g of compound 108, m.p. 70-71° C.

Workup

  1. additionAfter the addition
  2. extractionextracted with ethyl acetate
  3. washThe collected organic phases are washed with water and brine
  4. customdried
  5. customevaporated
  6. customCrystallization of the crude product from hexane

Sources & evidence

ORD record
ord-ab3bff9515c54efb92fe843555536023
Source dataset
uspto-grants-2010_10
Patent number
US07820865B2

Reaction notes

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