Methylparaben → HCID 14047213, compound

HRID 845709Notes

Reaction equation

HRID 845709 reaction equation
[OH-].[K+].[CH3:3][O:4][C:5]([C:7]1[CH:8]=[CH:9][C:10]([OH:13])=[CH:11][CH:12]=1)=[O:6].[CH3:14][C@@H:15]([CH2:31][CH3:32])[CH2:16][CH2:17][CH2:18]OC1C=C(S([O-])(=O)=O)C(C)=CC=1.CC(CC)CCCO>CO>[CH3:14][C@@H:15]([CH2:31][CH3:32])[CH2:16][CH2:17][CH2:18][O:13][C:10]1[CH:11]=[CH:12][C:7]([C:5]([O:4][CH3:3])=[O:6])=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 7456MethylparabenHCID 14797Potassium HydroxideHCID 983464-Methylhexan-1-olHCID 86742284HCID 86742284, compound

Product 1

HCID 14047213HCID 14047213, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

KOH (5 g, 0.09 mol) was added to a solution of methyl p-hydroxybenzoate (13.6 g, 0.09 mol) dissolved in methanol (66 ml), followed by dissolving these together on heating, adding (S)-p-(4-methylhexyloxy)toluenesulfonate (20 g, 0.07 mol) prepared from 4-methylhexanol in the same manner as in Example 1, (ii), heating the mixture under reflux for 10 hours, extracting the reaction mixture with toluene after completion of the reaction, distilling off the solvent, to obtain methyl (S)-p-(4-methylhexyloxy)benzoate (17 g), adding to a solution of this product dissolved in ethanol (7.5 ml), a solution of NaOH (4.9 g, 0.14 mol) dissolved in water (24.6 ml), heating the mixture under reflux for 5 hours, pouring the resulting reaction mixture into 6N-hydrochloric acid (90 ml) having the ice added, allowing the mixture to stand overnight, recrystallizing the resulting crystals from heptane to obtain (S)-p-(4-methylhexyloxy)benzoic acid (6.5 g), adding thionyl chloride (20 ml) to the benzoic acid (5 g, 0.02 mol), heating the mixture under reflux for one hour, and distilling off excess thionyl chloride to obtain p-(4-methylhexyloxy)benzoic acid chloride (XI) (5 g).

Workup

  1. dissolutionby dissolving these together
  2. temperatureon heating
  3. temperatureheating the mixture
  4. temperatureunder reflux for 10 hours
  5. extractionextracting the reaction mixture with toluene
  6. customafter completion of the reaction
  7. distillationdistilling off the solvent

Sources & evidence

ORD record
ord-54c427405ec2476cb0c4761b50bde5b4
Source dataset
uspto-grants-1988_07
Patent number
US04759869

Reaction notes

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