Hydrochloric Acid → 1-(4-Hydroxy-3,5-di-isopropylphenyl)-2-p-tolyloxy-ethanone

HRID 1163464

Reaction equation

HRID 1163464 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([O-:8])=[CH:4][CH:3]=1.[K+].Cl[CH2:11][C:12]([C:14]1[CH:19]=[C:18]([CH:20]([CH3:22])[CH3:21])[C:17]([OH:23])=[C:16]([CH:24]([CH3:26])[CH3:25])[CH:15]=1)=[O:13].Cl>CN(C)C=O>[OH:23][C:17]1[C:18]([CH:20]([CH3:22])[CH3:21])=[CH:19][C:14]([C:12](=[O:13])[CH2:11][O:8][C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=2)=[CH:15][C:16]=1[CH:24]([CH3:26])[CH3:25]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 23676568Potassium 4-methylphenolateHCID 858900592-Chloro-1-(4-hydroxy-3,5-di-isopropylphenyl)-ethanone

Product 1

HCID 577472281-(4-Hydroxy-3,5-di-isopropylphenyl)-2-p-tolyloxy-ethanoneYield 36%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 4.47 g (30.6 mmol) of potassium 4-methylphenolate in 150 ml of dimethyl-formamide a solution of 3.90 g (15.3 mmol) of 2-chloro-1-(4-hydroxy-3,5-di-isopropylphenyl)-ethanone in 70 ml dimethylformamide is added at room temperature within a period of 100 minutes. After additional 2 hours of stirring at room temperature the pH is adjusted to 6-7 with 1 N HCl and the mixture is extracted with ethyl acetate. The collected organic phases are washed with water, dried and evaporated. Crystallization of the crude product from ethyl acetate/hexane gives 1.8 g of compound 105, m.p. 124-125° C.

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. washThe collected organic phases are washed with water
  3. customdried
  4. customevaporated
  5. customCrystallization of the crude product from ethyl acetate/hexane

Sources & evidence

ORD record
ord-1397daaa6d5f4894b939af1dce66039d
Source dataset
uspto-grants-2010_10
Patent number
US07820865B2

Linked notes

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