Hydrochloric Acid → 2-(3,7-Dimethyl-oct-6-enyloxy]-1-(4-hydroxy-3,5-di-isopropyl-phenyl)-ethanone

HRID 1163468Notes

Reaction equation

HRID 1163468 reaction equation
[OH-].[K+].Cl[CH2:4][C:5]([C:7]1[CH:12]=[C:11]([CH:13]([CH3:15])[CH3:14])[C:10]([OH:16])=[C:9]([CH:17]([CH3:19])[CH3:18])[CH:8]=1)=[O:6].Cl.CN1[CH2:26][CH2:25][CH2:24][C:23]1=[O:27]>>[CH3:26][CH:25]([CH2:10][CH2:9][CH:8]=[C:7]([CH3:12])[CH3:5])[CH2:24][CH2:23][O:27][CH2:4][C:5]([C:7]1[CH:12]=[C:11]([CH:13]([CH3:15])[CH3:14])[C:10]([OH:16])=[C:9]([CH:17]([CH3:19])[CH3:18])[CH:8]=1)=[O:6]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 13387N-methyl-2-pyrrolidone2×HCID 14797Potassium HydroxideHCID 858900592-Chloro-1-(4-hydroxy-3,5-di-isopropylphenyl)-ethanone

Product 1

HCID 577472382-(3,7-Dimethyl-oct-6-enyloxy]-1-(4-hydroxy-3,5-di-isopropyl-phenyl)-ethanone

Procedure

To a solution of 4.69 g (30 mmol) of 3,7-dimethyl-oct-6-dien-1-ol and 4.21 g (75 mmol) of potassium hydroxide in 150 ml of N-methylpyrrolidone a solution of 3.82 g (15 mmol) of 2-chloro-1-(4-hydroxy-3,5-di-isopropylphenyl)-ethanone in 75 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 2.58 g of compound 109, m.p. 37-39° 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-89dc8ba449c14a96931127f0e9d1ccc9
Source dataset
uspto-grants-2010_10
Patent number
US07820865B2

Reaction notes

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