Sulfuric Acid → p-n-Octadecyloxybenzoic acid

HRID 21434

Reaction equation

HRID 21434 reaction equation
[CH2:1]([O:19][C:20]1[CH:29]=[CH:28][C:23]([C:24]([O:26]C)=[O:25])=[CH:22][CH:21]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].S(=O)(=O)(O)O>C(O)(=O)C>[CH2:1]([O:19][C:20]1[CH:21]=[CH:22][C:23]([C:24]([OH:26])=[O:25])=[CH:28][CH:29]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 4189536Methyl 4-(octadecyloxy)benzoate

Product 1

HCID 139993p-n-Octadecyloxybenzoic acidYield 82.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture containing methyl 4-octadecyloxybenzoate (30 g) and acetic acid (10 ml) was warmed until a solution was obtained. To this solution was added concentrated sulfuric acid (3 ml), and the mixture heated to slowly distill off the methyl acetate. This distillation was carried out over a period of 40 minutes. The solution was then cooled just below the boiling point and stirred for an additional 30 minutes. The hot reaction mixture was poured onto cold water and the solid filtered and dried. The product was then slurried in methylene chloride (100 ml) then filtered. The solid was recrystallized from 2-butanone to give 4-octadecyloxybenzoic acid (24 g).

Workup

  1. temperaturewas warmed until a solution
  2. customwas obtained
  3. temperaturethe mixture heated
  4. distillationto slowly distill off the methyl acetate
  5. distillationThis distillation
  6. temperatureThe solution was then cooled just below the boiling point
  7. additionThe hot reaction mixture was poured onto cold water
  8. filtrationthe solid filtered
  9. customdried
  10. filtrationthen filtered
  11. customThe solid was recrystallized from 2-butanone

Sources & evidence

ORD record
ord-2a7c3976ac664099ac53a5193537f233
Source dataset
uspto-grants-1995_06
Patent number
US05424183

Linked notes

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