Water → HCID 21418526, compound

HRID 596318Notes

Reaction equation

HRID 596318 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1.[OH-].[Na+].O.[CH3:20][O:21][C:22]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:23]=1[C:24](Cl)=[O:25]>O1CCOCC1>[CH3:20][O:21][C:22]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:23]=1[C:24]([NH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)=[O:25]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 123841765-Chloro-2-methoxybenzoyl chlorideHCID 14850211HCID 14850211, compound

Product 1

HCID 21418526HCID 21418526, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 43 gm (20.1 millimols) of 4-[2-Aminoethyl]-4'-hydroxy-biphenyl in a mixture of 8.5 gm (21.3 millimols) of sodium hydroxide, 270 ml of water and 100 ml of dioxane, was acylated with 41.5 gm (20.1 millimols) of 2-methoxy-5-chloro-benzoyl chloride at 0° C. After stirring at room temperature for 2 hours, the mixture was extracted with chloroform, and the organic phase was dried over sodium sulfate. After distilling off the extracting agent, 72 gm (94% of theory) of a light yellow oil were obtained. This oil crystallized slowly and was uniform in the thin-layer chromatogram (silicagel; eluant: benzene/ethyl acetate = 7:2). After purification by column chromatography on silicagel with benzene/ethyl acetate as the eluant, the oil crystallized slowly. M.p. 169° C

Workup

  1. extractionthe mixture was extracted with chloroform
  2. dry with materialthe organic phase was dried over sodium sulfate
  3. distillationAfter distilling off the extracting agent, 72 gm (94% of theory) of a light yellow oil
  4. customwere obtained
  5. customThis oil crystallized slowly
  6. customAfter purification by column chromatography on silicagel with benzene/ethyl acetate as the eluant
  7. customthe oil crystallized slowly

Sources & evidence

ORD record
ord-f415c82079e84c3cb9434c3d3a437cd3
Source dataset
uspto-grants-1977_03
Patent number
US04010279

Reaction notes

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