Sodium hydride → HCID 22168537, compound

HRID 1709940Notes

Reaction equation

HRID 1709940 reaction equation
[CH3:1][C:2]([CH2:4][C:5]1[CH:6]=[CH:7][C:8]([OH:11])=[CH:9][CH:10]=1)=[O:3].[H-].[Na+].[Cl:14][CH2:15][CH2:16][CH2:17]I>CN(C)C=O.CCCCCC.C(OCC)C>[Cl:14][CH2:15][CH2:16][CH2:17][O:11][C:8]1[CH:7]=[CH:6][C:5]([CH2:4][C:2](=[O:3])[CH3:1])=[CH:10][CH:9]=1

Participants

7

Reactant 3

HCID 24758Sodium hydrideHCID 813631-Chloro-3-iodopropaneHCID 70192744-Hydroxyphenylacetone

Product 1

HCID 22168537HCID 22168537, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Procedure

A 4.50 g portion of p-hydroxyphenylacetone, prepared above, was dissolved in 80 mL of anhydrous dimethylformamide under a dry nitrogen atmosphere. With stirring 1.26 g of sodium hydride (as a 60% dispersion in oil) was added to the solution. After 3 minutes, 9.40 g of 1-chloro-3-iodopropane was quickly added. After stirring for approximately 18 hours, the reaction was diluted with 300 mL hexane and 100 mL diethyl ether. The resulting mixture was washed with distilled water, 5% sodium hydroxide solution, and brine. The remaining organic phase was dried and evaporated to dryness in vacuo. The yellow oil was purified by column chromatography over silica gel, using 22% ethyl acetate and 78% hexane. Appropriate fractions were pooled and solvents removed in vacuo to yield 3.06 g of a yellow oil.

Workup

  1. additionwas added to the solution
  2. washThe resulting mixture was washed with distilled water, 5% sodium hydroxide solution, and brine
  3. customThe remaining organic phase was dried
  4. customevaporated to dryness in vacuo
  5. customThe yellow oil was purified by column chromatography over silica gel
  6. customsolvents removed in vacuo

Sources & evidence

ORD record
ord-bda53494758546dea79315716fb21d5b
Source dataset
uspto-grants-1990_08
Patent number
US04952336

Reaction notes

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