Hydrochloric Acid → HCID 11554936, compound

HRID 1158150Notes

Reaction equation

HRID 1158150 reaction equation
[OH-].[Na+].[C:3]([C:7]1[CH:8]=[C:9]([C:18]2[CH:19]=[C:20]([C:30]3[CH:35]=[CH:34][C:33]([C:36]([O:38]CC)=[O:37])=[CH:32][CH:31]=3)[CH:21]=[CH:22][C:23]=2[O:24][CH2:25][CH2:26][CH2:27][CH2:28][OH:29])[CH:10]=[CH:11][C:12]=1[N:13]([CH2:16][CH3:17])[CH2:14][CH3:15])([CH3:6])([CH3:5])[CH3:4].Cl>O1CCCC1.O.CCCCCCC>[C:3]([C:7]1[CH:8]=[C:9]([C:18]2[CH:19]=[C:20]([C:30]3[CH:31]=[CH:32][C:33]([C:36]([OH:38])=[O:37])=[CH:34][CH:35]=3)[CH:21]=[CH:22][C:23]=2[O:24][CH2:25][CH2:26][CH2:27][CH2:28][OH:29])[CH:10]=[CH:11][C:12]=1[N:13]([CH2:14][CH3:15])[CH2:16][CH3:17])([CH3:5])([CH3:6])[CH3:4]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 11627728HCID 11627728, compound

Product 1

HCID 11554936HCID 11554936, compoundYield 82.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 8900HeptaneSolvent

Procedure

0.9 mL of aqueous 1N sodium hydroxide solution is added to a solution of 300 mg of ethyl 3″-tert-butyl-4″-diethylamino-4′-(4-hydroxybutoxy)-[1,1′;3′,1″]terphenyl-4-carboxylate (Example 2b) in a mixture of 10 mL of tetrahydrofuran and 3 mL of water. The reaction medium is stirred at room temperature for 12 hours. 0.5 mL of aqueous 1N sodium hydroxide solution is then added. After 12 hours at room temperature, the reaction medium is heated to 50° C. and then left at room temperature for 3 days. The reaction is stopped by adding 5 mL of water. The reaction medium is acidified to pH 5 by adding aqueous 1N hydrochloric acid solution and is then extracted with ethyl acetate. The organic phase is dried over magnesium sulfate. The solid obtained is taken up in heptane and then filtered. 235 mg of 3″-tert-butyl-4″-diethylamino-4′-(4-hydroxybutoxy)-[1,1′;3′,1″]terphenyl-4-carboxylic acid are obtained in the form of a white solid (yield=83%, m.p.=165° C.).

Workup

  1. waitAfter 12 hours at room temperature
  2. temperaturethe reaction medium is heated to 50° C.
  3. waitleft at room temperature for 3 days
  4. extractionis then extracted with ethyl acetate
  5. dry with materialThe organic phase is dried over magnesium sulfate
  6. customThe solid obtained
  7. filtrationfiltered

Sources & evidence

ORD record
ord-9a2c2f719836400c9016fc3c27eb5918
Source dataset
uspto-grants-2010_10
Patent number
US07807708B2

Reaction notes

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