Acetic Acid → HCID 11539622, compound

HRID 1261547Notes

Reaction equation

HRID 1261547 reaction equation
C([O:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18](C3C(C(OCC)=O)=CC=CC=3)=[CH:17][CH:16]=2)=[CH:11][C:10]=1[C:32]1[CH:37]=[CH:36][C:35]([NH:38][CH2:39][CH3:40])=[C:34]([C:41]([CH3:44])([CH3:43])[CH3:42])[CH:33]=1)(=O)C.[OH-].[Na+].O.[C:48]([OH:51])(=[O:50])C>C(O)C>[C:41]([C:34]1[CH:33]=[C:32]([C:10]2[CH:11]=[C:12]([C:15]3[CH:16]=[CH:17][C:18]([C:48]([OH:51])=[O:50])=[CH:19][CH:20]=3)[CH:13]=[CH:14][C:9]=2[O:8][CH2:7][CH2:6][CH2:5][OH:4])[CH:37]=[CH:36][C:35]=1[NH:38][CH2:39][CH3:40])([CH3:44])([CH3:42])[CH3:43]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962Water2×HCID 14798Sodium HydroxideHCID 66671940HCID 66671940, compound

Product 1

HCID 11539622HCID 11539622, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

900 mg (1.74 mmol; 1 eq.) of ethyl 4′-(3-acetoxypropoxy)-3″-tert-butyl-4″-ethylamino-[1,1′;3′,1″]terphenyl-4-benzoate are dissolved in 10 ml of absolute ethanol. 312 mg (7.8 mmol; 4.5 eq.) of sodium hydroxide and 4 ml of H2O are added at room temperature and the mixture is then heated to reflux. These conditions are maintained for about 1 hour 30 minutes. The reaction medium is concentrated to a small volume; H2O is added to the precipitate formed, and the mixture is then acidified with acetic acid to pH ˜4-5. This suspension is fluidized by adding H2O and stirred at room temperature for 1 hour. The resulting mixture is filtered through a sinter funnel, rinsed with H2O until the filtrate is neutral, and oven-dried. 694 mg of 3″-tert-butyl-4″-ethylamino-4′-(3-hydroxypropoxy)-[1,1′;3′,1″]terphenyl-4-carboxylic acid are thus obtained in the form of a white powder (yield=89%).

Workup

  1. temperaturethe mixture is then heated to reflux
  2. temperatureThese conditions are maintained for about 1 hour 30 minutes
  3. concentrationThe reaction medium is concentrated to a small volume
  4. additionH2O is added to the precipitate
  5. customformed
  6. filtrationThe resulting mixture is filtered through a sinter funnel
  7. washrinsed with H2O until the filtrate
  8. customoven-dried

Sources & evidence

ORD record
ord-429a77d8e000408582c195c7c4d70f25
Source dataset
uspto-grants-2013_06
Patent number
US08470871B2

Reaction notes

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