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

HRID 248013Notes

Reaction equation

HRID 248013 reaction equation
C[O:2][C:3](=[O:26])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[C:6]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH:5]=1.[OH-].[K+].O.Cl>C(O)C>[CH2:19]([O:18][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][CH3:17])[C:3]([OH:26])=[O:2])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 540951973,4-Bis(heptyloxy)benzoic acid methyl ester

Product 1

HCID 190152233,4-Bis(heptyloxy)benzoic acidYield 93.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 25 g of product from Example 109, 11.54 g of potassium hydroxide, 30 ml of water and 500 ml ethyl alcohol is heated at reflux temperature for 24 hours. The reaction mixture is cooled and maintained at room temperature for 48 hours. The mixture is acidified to pH 2 with concentrated hydrochloric acid, concentrated in vacuo, diluted with water and extracted with chloroform. The combined chloroform extracts are washed with saturated sodium chloride, dried and concentrated in vacuo to give 22.58 g of the desired product as colorless crystals.

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature for 24 hours
  3. temperatureThe reaction mixture is cooled
  4. concentrationconcentrated in vacuo
  5. additiondiluted with water
  6. extractionextracted with chloroform
  7. washThe combined chloroform extracts are washed with saturated sodium chloride
  8. customdried
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7d4d19d8acd544a18e237dcf5b24b335
Source dataset
uspto-grants-1993_05
Patent number
US05208247

Reaction notes

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