Potassium Hydroxide → Benzoic acid, 3,5-bis(dodecyloxy)-

HRID 1917588Notes

Reaction equation

HRID 1917588 reaction equation
[CH2:1]([O:13][C:14]1[CH:15]=[C:16]([CH:21]=[C:22]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH:23]=1)[C:17]([O:19]C)=[O:18])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[OH-].[K+]>CCO>[CH2:25]([O:24][C:22]1[CH:21]=[C:16]([CH:15]=[C:14]([O:13][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH:23]=1)[C:17]([OH:19])=[O:18])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 58788081HCID 58788081, compound

Product 1

HCID 12150452Benzoic acid, 3,5-bis(dodecyloxy)-Yield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl 3,5-bis-dodecyloxybenzoate (8 g) was refluxed for 6 h with EtOH (25 mL) and 10% KOH. Then, the mixture was cooled and poured onto ice H2O and extracted with MC, then the organic layer was stored over dry MgSO4. The solvent was removed; the crude was recrystallized in EtOH to yield 85% of the benzoic acid product as a white solid. 1H-NMR (300 MHz, CDCl3) δ 7.1 (d, 2H), 6.6 (t, 1H), 4.0 (t, 4H), 1.7-1.8 (m, 4H), 1.4-1.6 (m, 4H), 1.2-1.3 (m, 32H), 0.9 (t, 6H).

Workup

  1. temperatureThen, the mixture was cooled
  2. additionpoured onto ice H2O
  3. extractionextracted with MC
  4. customThe solvent was removed
  5. customthe crude was recrystallized in EtOH

Sources & evidence

ORD record
ord-ea2df028c6fe41a6b90045367c15bbca
Source dataset
uspto-grants-2013_12
Patent number
US08618298B2

Reaction notes

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