Hydrochloric Acid → HCID 178455777, compound

HRID 1857899Notes

Reaction equation

HRID 1857899 reaction equation
[OH-].[K+].[OH:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10]C)=[O:9])=[CH:6][CH:5]=1.[CH2:14]([C@H:16]1[CH2:21][CH2:20][C@H:19]([CH2:22]Br)[CH2:18][CH2:17]1)[CH3:15].[OH-].[Na+].Cl>O>[CH2:14]([C@H:16]1[CH2:21][CH2:20][C@H:19]([CH2:22][O:3][C:4]2[CH:13]=[CH:12][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=2)[CH2:18][CH2:17]1)[CH3:15]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 7456MethylparabenHCID 14797Potassium HydroxideHCID 14798Sodium HydroxideHCID 178455729HCID 178455729, compound

Product 1

HCID 178455777HCID 178455777, compoundYield 57.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of potassium hydroxide (56.1 g) dissolved in 30 ml of water, and methyl 4-hydroxybenzoate (152 g) were suspended in 1500 ml of ethyleneglycolmonoethylether. To this mixture was dropped trans-4-ethylcyclohexylmethylbromide (200 g), and then the mixture formed was stirred under reflux for 4 hours. After cooling to room temperature, a solution of sodium hydroxide (80 g) dissolved in water (400 ml) was added with stirring and was refluxed for 2 hours. After the reaction was completed, the mixture was cooled, added with diluted hydrochloric acid (1 liter), and extracted with toluene (5 liters). The organic layer separated was washed with water, dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure to obtain 4-(trans-4-ethylcyclohexylmethoxy)benzoic acid (147 g).

Workup

  1. customthe mixture formed
  2. temperatureunder reflux for 4 hours
  3. additionwas added
  4. stirringwith stirring
  5. temperaturewas refluxed for 2 hours
  6. temperaturethe mixture was cooled
  7. extractionextracted with toluene (5 liters)
  8. customThe organic layer separated
  9. washwas washed with water
  10. dry with materialdried over anhydrous magnesium sulfate
  11. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-067b0ae94b564ff0bf98ec824aa11276
Source dataset
uspto-grants-2000_11
Patent number
US06149990

Reaction notes

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