Methylparaben → HCID 54331531, compound

HRID 1788770Notes

Reaction equation

HRID 1788770 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]([CH:14]([CH2:17][CH2:18][CH2:19][CH3:20])[CH2:15]Cl)[CH3:13].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][CH2:15][CH:14]([CH2:12][CH3:13])[CH2:17][CH2:18][CH2:19][CH3:20])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 7456MethylparabenHCID 312403-(Chloromethyl)-heptaneHCID 10942334Sodium Methoxide

Product 1

HCID 54331531HCID 54331531, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 51.7 g (0.34 mol) of 4-hydroxybenzoic acid methylester, 500 ml of dimethyl formamide, 60 g (0.40 mol) of 2-ethylhexylchloride and 21.8 g (0.40 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 under reduced pressure. The residue was dissolved in methylene chloride and chromatographed (eluent: methylene chloride) on silica gel (Merck) to yield 43 g (48% of the theoretical) of 4-(2-ethylhexyloxy)benzoic acid methylester. A refractive index of

Workup

  1. temperaturewas heated for 7 hours
  2. temperatureafter cooling
  3. customremoval of the sodium chloride
  4. filtrationby filtration
  5. customwas evaporated to dryness under reduced pressure
  6. dissolutionThe residue was dissolved in methylene chloride
  7. customchromatographed (eluent: methylene chloride) on silica gel (Merck)

Sources & evidence

ORD record
ord-145a27aebfd74767a69e19e03a8c59f6
Source dataset
uspto-grants-1987_08
Patent number
US04684665

Reaction notes

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