Hydrochloric Acid → HCID 57747239, compound

HRID 1163470Notes

Reaction equation

HRID 1163470 reaction equation
[CH3:1][C:2]([OH:11])([CH2:5][CH2:6][CH:7]=[C:8]([CH3:10])[CH3:9])[CH:3]=[CH2:4].[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]([CH:3]=[CH2:4])([O:11][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])[CH2:5][CH2:6][CH:7]=[C:8]([CH3:10])[CH3:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6549LinaloolHCID 14797Potassium HydroxideHCID 858900592-Chloro-1-(4-hydroxy-3,5-di-isopropylphenyl)-ethanone

Product 1

HCID 57747239HCID 57747239, compoundYield 2.2%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent2×

Procedure

To a solution of 12.7 g (79 mmol) of 3,7-dimethyl-octa-1,6-dien-3-ol and 10.9 g (195 mmol) of potassium hydroxide in 80 ml of N-methylpyrrolidone a solution of 10.0 g (39 mmol) of 2-chloro-1-(4-hydroxy-3,5-di-isopropylphenyl)-ethanone in 120 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 0.32 g of compound III, m.p. 71-72° 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-46a8d3bbbf4946f9a4395081d70854db
Source dataset
uspto-grants-2010_10
Patent number
US07820865B2

Reaction notes

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