Hydrochloric Acid → 3-(1,1-Dimethylethyl)-4-(tetradecyloxy)benzoic acid

HRID 1728816Notes

Reaction equation

HRID 1728816 reaction equation
C[O:2][C:3](=[O:29])[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]([C:25]([CH3:28])([CH3:27])[CH3:26])[CH:5]=1.[OH-].[K+].Cl.C(Cl)(Cl)Cl>CO.C(O)C.O>[CH3:28][C: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:29])=[O:2])([CH3:26])[CH3:27]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6212ChloroformHCID 14797Potassium HydroxideHCID 538584113-(1,1-Dimethylethyl)-4-(tetradecyloxy)benzoic acid methyl ester

Product 1

HCID 190150743-(1,1-Dimethylethyl)-4-(tetradecyloxy)benzoic acidYield 88.7%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 36.2 g Of product from Example 31 in 320 ml of methyl alcohol, 125 ml ethyl alcohol, 20 ml of water and 15 g of potassium hydroxide is mechanically stirred at reflux temperature for 41/2 hours. The reaction is cooled and 325 ml of 1N hydrochloric acid and 200 ml of chloroform is added. The mixture is heated until homogeneous, the layers are separated and extracted with chloroform. The combined organic layers are washed with 1N hydrochloric acid, dried and concentrated in vacuo. The residue is recrystallized from chloroform/hexane to give 31 g of the product as white crystals.

Workup

  1. temperatureat reflux temperature for 41/2 hours
  2. temperatureThe reaction is cooled
  3. temperatureThe mixture is heated until homogeneous, the layers
  4. customare separated
  5. extractionextracted with chloroform
  6. washThe combined organic layers are washed with 1N hydrochloric acid
  7. customdried
  8. concentrationconcentrated in vacuo
  9. customThe residue is recrystallized from chloroform/hexane

Sources & evidence

ORD record
ord-a01bc04ae9e54614a2e08a6ef470f68c
Source dataset
uspto-grants-1994_07
Patent number
US05328921

Reaction notes

Loading…