Methylparaben → Methyl 4-(octadecyloxy)benzoate

HRID 21433

Reaction equation

HRID 21433 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[CH2:12](Br)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH2:29]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=1)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH3:12]

Participants

5

Reactant 3

HCID 7456MethylparabenHCID 82181-BromooctadecaneHCID 11430Potassium Carbonate

Product 1

HCID 4189536Methyl 4-(octadecyloxy)benzoateYield 45.4%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture containing methyl 4-hydroxybenzoate (45.6 g), octadecylbromide (100 g), and potassium carbonate (41.4 g) in 2-butanone (200 ml) was heated at reflux for 16 hours. The solvent was then removed until 125 ml of 2-butanone had been collected. While it was still warm, the remaining material was poured into methanol (400 ml). The product was filtered and recrystallized from 2000 ml of methanol to give methyl 4-octadecyloxybenzoate (55 g).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 hours
  3. customThe solvent was then removed until 125 ml of 2-butanone
  4. customhad been collected
  5. temperatureWhile it was still warm
  6. additionthe remaining material was poured into methanol (400 ml)
  7. filtrationThe product was filtered
  8. customrecrystallized from 2000 ml of methanol

Sources & evidence

ORD record
ord-5bd9025ada774765b81d784d3b0ccf52
Source dataset
uspto-grants-1995_06
Patent number
US05424183

Linked notes

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