Hydrochloric Acid → 3,4-Bis(tetradecyloxy)benzoic acid

HRID 248010Notes

Reaction equation

HRID 248010 reaction equation
C[O:2][C:3](=[O:40])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[C:6]([O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[CH:5]=1.[OH-].[K+].O.Cl>C(O)C>[CH2:26]([O:25][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][C:7]=1[O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[C:3]([OH:40])=[O:2])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 120485573,4-Bis(tetradecyloxy)benzoic acid methyl ester

Product 1

HCID 190162583,4-Bis(tetradecyloxy)benzoic acidYield 100.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 35 g of product from Example 103, 7.5 g of potassium hydroxide, 30 ml of water and 500 ml of ethyl alcohol is heated at reflux for 24 hours. The reaction is then stirred at room temperature for 48 hours and acidified to pH 2 with concentrated hydrochloric acid. The mixture is concentrated in vacuo, diluted with water and extracted with chloroform. The combined organic layers are washed with saturated sodium chloride, dried and concentrated in vacuo to give 34.2 g of the desired product.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 24 hours
  3. concentrationThe mixture is concentrated in vacuo
  4. additiondiluted with water
  5. extractionextracted with chloroform
  6. washThe combined organic layers are washed with saturated sodium chloride
  7. customdried
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2b648ebf29584bcfa1919f1fd622cfa9
Source dataset
uspto-grants-1993_05
Patent number
US05208247

Reaction notes

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