Hydrochloric Acid → HCID 21451950, compound

HRID 596320Notes

Reaction equation

HRID 596320 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+].[CH3:19][O:20][C:21]1[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=1[C:23](Cl)=[O:24].Cl>O1CCOCC1.O.O1CCOCC1>[CH3:19][O:20][C:21]1[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=1[C:23]([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:24]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 889692-Methoxybenzoyl chlorideHCID 14850211HCID 14850211, compound

Product 1

HCID 21451950HCID 21451950, compound

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

A solution of 9 gm (42 millimols) of 4-[2-aminoethyl]-4'-hydroxy-biphenyl in a solution of 1.72 gm (43 millimols) of sodium hydroxide in 100 ml of a mixture of water/dioxane (1:1) was acylated at 0° C with a solution of 13 gm (76 millimols) of 2-methoxybenzoyl chloride in 50 ml of dioxane, while maintaining the pH at 10 by periodic addition of sodium hydroxide. After all of the acid chloride had been added, the mixture was stirred at room temperature for 2 hours, and then the pH of the resulting suspension was adjusted to between 4 and 5 by addition of 2 N hydrochloric acid. The suspension was now extracted with chloroform. After extraction with a dilute sodium bicarbonate solution, the chloroform phase was dried with sodium sulfate, evaporated, and the residue was recrystallized from ethyl acetate. Yield: 8.7 gm (59% of theory); m.p. 118° C.

Workup

  1. temperaturewhile maintaining the pH at 10
  2. extractionThe suspension was now extracted with chloroform
  3. extractionAfter extraction with a dilute sodium bicarbonate solution
  4. dry with materialthe chloroform phase was dried with sodium sulfate
  5. customevaporated
  6. customthe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-e79398456ced455584319193b667a8cb
Source dataset
uspto-grants-1977_03
Patent number
US04010279

Reaction notes

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