Hydrochloric Acid → 3''-Tert-butyl-4''-diethylamino-4'-(2-hydroxyethoxy)-[1,1';3',1'']terphenyl-4-carboxylic acid

HRID 1516637Notes

Reaction equation

HRID 1516637 reaction equation
C([O:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([O:22]CC)=[O:21])=[CH:16][CH:15]=2)=[CH:10][C:9]=1[C:25]1[CH:30]=[CH:29][C:28]([N:31]([CH2:34][CH3:35])[CH2:32][CH3:33])=[C:27]([C:36]([CH3:39])([CH3:38])[CH3:37])[CH:26]=1)(=O)C.[OH-].[Na+].[Cl-].[NH4+].Cl>O1CCCC1>[C:36]([C:27]1[CH:26]=[C:25]([C:9]2[CH:10]=[C:11]([C:14]3[CH:19]=[CH:18][C:17]([C:20]([OH:22])=[O:21])=[CH:16][CH:15]=3)[CH:12]=[CH:13][C:8]=2[O:7][CH2:6][CH2:5][OH:4])[CH:30]=[CH:29][C:28]=1[N:31]([CH2:32][CH3:33])[CH2:34][CH3:35])([CH3:38])([CH3:39])[CH3:37]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 66672106Ethyl 4'-(2-acetoxyethoxy)-3''-tert-butyl-4''-diethylamino[1,1';3',1'']terphenyl-4-carboxylate

Product 1

HCID 115471313''-Tert-butyl-4''-diethylamino-4'-(2-hydroxyethoxy)-[1,1';3',1'']terphenyl-4-carboxylic acidYield 51.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1 g (1.9 mmol) of ethyl 4′-(2-acetoxyethoxy)-3″-tert-butyl-4″-diethylamino[1,1′;3′,1″]terphenyl-4-carboxylate is placed in 50 mL of tetrahydrofuran and 19 mL (19 mmol) of 1N sodium hydroxide solution are added. The mixture is stirred at reflux for 12 hours. The yellow solution obtained is poured into saturated ammonium chloride solution, the pH is adjusted to 5-6 with 1N hydrochloric acid solution and the mixture is then extracted with ethyl acetate. The organic phase is dried over magnesium sulfate and then concentrated to dryness. 455 mg of 3″-tert-butyl-4″-diethylamino-4′-(2-hydroxyethoxy)-[1,1′;3′,1″]terphenyl-4-carboxylic acid are obtained in the form of a white solid (yield=52%, m.p.=216° C.)

Workup

  1. temperatureat reflux for 12 hours
  2. customThe yellow solution obtained
  3. extractionthe mixture is then extracted with ethyl acetate
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-61671c707cd64522a87d76751754e8f9
Source dataset
uspto-grants-2012_07
Patent number
US08227507B2

Reaction notes

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