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

HRID 1261522Notes

Reaction equation

HRID 1261522 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-eac53fd484dc4744a0eb3e9f0497e9c0
Source dataset
uspto-grants-2013_06
Patent number
US08470871B2

Reaction notes

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