Hydrochloric Acid → 4-(1-Methylbutoxy)benzoic acid

HRID 1762774Notes

Reaction equation

HRID 1762774 reaction equation
COC(=O)C1C=CC(O)=CC=1.[OH-].[K+].CC(OS(C1C=CC(C)=CC=1)(=O)=O)CCC.Cl.C[O:32][C:33](=[O:46])[C:34]1[CH:39]=[CH:38][C:37]([O:40][CH:41]([CH3:45])[CH2:42][CH2:43][CH3:44])=[CH:36][CH:35]=1.[OH-].[Na+]>CO.C(O)C.O.C1(C)C=CC=CC=1>[CH3:45][CH:41]([O:40][C:37]1[CH:36]=[CH:35][C:34]([C:33]([OH:46])=[O:32])=[CH:39][CH:38]=1)[CH2:42][CH2:43][CH3:44]

Participants

11

Reactant 6

HCID 313Hydrochloric Acid2×HCID 7456MethylparabenHCID 14797Potassium HydroxideHCID 14798Sodium HydroxideHCID 997532-Pentanol, 2-(4-methylbenzenesulfonate)HCID 20095113p-(1-Methyl-butyloxy)benzoic acid methyl ester

Product 1

HCID 52586714-(1-Methylbutoxy)benzoic acid

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

On the other hand, p-hydroxybenzoic acid methyl ester (28.5 g, 0.187 mol) was dissolved in methanol (120 ml), followed by adding and dissolving KOH (10.1 g, 0.187 mol), adding to the solution, optically active p-toluenesulfonic acid 1-methyl-butyl ester obtained above (50 g, 0.206 mol), keeping the mixture under reflux for 4 hours, cooling, adding toluene (200 ml) and 6N-HCl (50 ml), washing the toluene layer with 2N-NaOH aqueous solution, then with water till the washing water became neutral, and distilling off toluene to obtain as a residue, optically active p-(1-methyl-butyloxy)benzoic acid methyl ester (16.6 g, 0.070 mol), which was then dissolved in ethanol (5 ml), NaOH (4.2 g, 0.105 mol) and water (21 ml), heating under reflux for one hour, cooling, pouring the reaction solution in 6N-HCl aqueous solution (50 ml) with stirring, separating deposited crystals by filtration, and recrystallizing from ethanol to obtain optically active p-(1-methyl-butyloxy)benzoic acid having a m.p. of 67.0°~68.8° C. (9.3 g). To this product (6.5 g, 0.031 mol) was added thionyl chloride (6.0 g, 0.047 mol), followed by heating under reflux for one hour and distilling off excess thionyl chloride to obtain optically active p-(1-methyl-butyloxy)benzoic acid chloride (6.2 g).

Workup

  1. additionby adding
  2. customobtained above (50 g, 0.206 mol)
  3. temperatureunder reflux for 4 hours
  4. temperaturecooling
  5. washwashing the toluene layer with 2N-NaOH aqueous solution
  6. distillationdistilling off toluene
  7. customto obtain as a residue
  8. temperatureunder reflux for one hour
  9. temperaturecooling
  10. customseparating
  11. filtrationby filtration
  12. customrecrystallizing from ethanol

Sources & evidence

ORD record
ord-3712b553e7c04e15b213d551b5a53dd0
Source dataset
uspto-grants-1989_05
Patent number
US04834907

Reaction notes

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