Hydrochloric Acid → HCID 67425364, compound

HRID 1163472Notes

Reaction equation

HRID 1163472 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[O-:12].[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].C(N(CC)CC)C.Cl>O.CN(C)C=O>[OH:27][C:21]1[C:22]([CH:24]([CH3:26])[CH3:25])=[CH:23][C:18]([C:16](=[O:17])[CH2:15][O:12][N:3]2[C:4](=[O:11])[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[C:2]2=[O:1])=[CH:19][C:20]=1[CH:28]([CH3:30])[CH3:29]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 23678638HCID 23678638, compoundHCID 858900592-Chloro-1-(4-hydroxy-3,5-di-isopropylphenyl)-ethanone

Product 1

HCID 67425364HCID 67425364, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3.03 g (15 mmol) of potassium 1,3-dioxo-1,3-dihydro-isoindol-2-olate [prepared according to P. Consonni, D Favara, A. Omodei-Salé, G. Bartolini, A. Ricci, J. Chem. Soc., Perkin Trans. 2, 1983, 967-973], 3.82 g (15 mmol) of 2-chloro-1-(4-hydroxy-3,5-di-iso-propyl-phenyl)-ethanone, 2.3 ml of triethylamine and 100 ml of dimethylformamide is stirred at room temperature and under nitrogen atmosphere for 1.5 hours. Then the mixture is poured onto 500 ml of water containing 9 ml of 2N HCl and is extracted with ethyl acetate. The collected organic phases are washed with water, dried and evaporated. The resulting crude product is recrystallized from ethyl acetate and hexane to give 2.52 g of compound 114, m.p. 136-139°.

Workup

  1. customprepared
  2. extractionis extracted with ethyl acetate
  3. washThe collected organic phases are washed with water
  4. customdried
  5. customevaporated
  6. customThe resulting crude product is recrystallized from ethyl acetate and hexane

Sources & evidence

ORD record
ord-49e0c36263834fd191175af0ace28942
Source dataset
uspto-grants-2010_10
Patent number
US07820865B2

Reaction notes

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