Hydrochloric Acid → 3,4,5-Tris((11,13-tetradecadienyl)oxy)benzoic acid

HRID 1695077Notes

Reaction equation

HRID 1695077 reaction equation
[CH2:1]([O:15][C:16]1[CH:17]=[C:18]([CH:22]=[C:23]([O:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH:51]=[CH:52][CH:53]=[CH2:54])[C:24]=1[O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH:36]=[CH:37][CH:38]=[CH2:39])[C:19]([O-:21])=[O:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]=[CH:12][CH:13]=[CH2:14].[OH-].[Na+].Cl>C(O)C.O>[CH2:41]([O:40][C:23]1[CH:22]=[C:18]([CH:17]=[C:16]([O:15][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]=[CH:12][CH:13]=[CH2:14])[C:24]=1[O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH:36]=[CH:37][CH:38]=[CH2:39])[C:19]([OH:21])=[O:20])[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH:51]=[CH:52][CH:53]=[CH2:54]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86615120HCID 86615120, compound

Product 1

HCID 866151193,4,5-Tris((11,13-tetradecadienyl)oxy)benzoic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

In the next step as shown in FIG. 18, the yellow oil prepared above, 3,4,5-tris((11,13-tetradecadienyl)oxy)benzoate, was dissolved in a solution of ethanol (400 mL), H2O (80 mL), and NaOH (3.21 g, 80.2 mmol) in a round-bottom flask equipped with a reflux condenser and a magnetic stir bar. The mixture was then stirred and refluxed at 80° C. for 12 hours. After this period, the solution was cooled to 0° C. using an ice bath and acidified to pH 5.0 with hydrochloric acid (42 mL, 3M) to afford a pale brown precipitate. The precipitate was then filtered, washed with hexane (2×100 mL), and dried overnight under vacuum to collect a white solid.

Workup

  1. customequipped with a reflux condenser and a magnetic stir bar
  2. waitAfter this period
  3. temperaturethe solution was cooled to 0° C.
  4. customto afford a pale brown precipitate
  5. filtrationThe precipitate was then filtered
  6. washwashed with hexane (2×100 mL)
  7. customdried overnight under vacuum
  8. customto collect a white solid

Sources & evidence

ORD record
ord-9b60995795e245f395f13d0450ce2af1
Source dataset
uspto-grants-2012_04
Patent number
US08163204B2

Reaction notes

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