Methylparaben → HCID 53712475, compound

HRID 1788771Notes

Reaction equation

HRID 1788771 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[CH2:12]([O:24][CH2:25][CH2:26]Cl)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].C[O-].[Na+]>CN(C)C=O>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:26][CH2:25][O:24][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 7456MethylparabenHCID 5455631-chloro-2-dodecyloxyethaneHCID 10942334Sodium Methoxide

Product 1

HCID 53712475HCID 53712475, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 20.4 g (0.134 mol) of 4-hydroxybenzoic acid methylester, 200 ml of dimethyl formamide, 40 g (0.160 mol) of 2-dodecyloxy ethylchloride (from 2-dodecyloxy ethanol and thionyl chloride) and 8.6 g (0.160 mol) of sodium methylate was heated for 7 hours to boiling temperature and, after cooling and removal of the sodium chloride by filtration, was evaporated to dryness. The residue was dissolved in methylene chloride and subjected to column chromatography (silica gel, Merck using methylene chloride as the eluent). After recrystallization from methanol, the combined fractions after TLC gave 30 g (61% of the theoretical) of pure 4-(2-dodecyloxyethoxy)-benzoic acid methylester melting at 40° to 42° C.

Workup

  1. temperaturewas heated for 7 hours
  2. temperatureafter cooling
  3. customremoval of the sodium chloride
  4. filtrationby filtration
  5. customwas evaporated to dryness
  6. dissolutionThe residue was dissolved in methylene chloride
  7. customAfter recrystallization from methanol

Sources & evidence

ORD record
ord-b51e3c45dce24bd2a8edaa79ca6d4094
Source dataset
uspto-grants-1987_08
Patent number
US04684665

Reaction notes

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