Methylparaben → HCID 20571321, compound

HRID 261904Notes

Reaction equation

HRID 261904 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.[OH-:12].[Na+].[C:14]1([O-:20])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.Cl[CH2:22][C:23]1[C:28]([Br:29])=[C:27]([Br:30])[C:26]([CH2:31]Cl)=[C:25]([Br:33])[C:24]=1[Br:34].[CH3:35][O:36][CH2:37]CO>O>[C:3]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:22][C:23]2[C:28]([Br:29])=[C:27]([Br:30])[C:26]([CH2:31][O:20][C:14]3[CH:19]=[CH:18][C:17]([C:37]([O:36][CH3:35])=[O:12])=[CH:16][CH:15]=3)=[C:25]([Br:33])[C:24]=2[Br:34])=[CH:6][CH:5]=1)([O:2][CH3:1])=[O:11]

Participants

7

Reactant 5

HCID 7456MethylparabenHCID 80192-MethoxyethanolHCID 14798Sodium HydroxideHCID 119047PhenolateHCID 30160891,2,4,5-Tetrabromo-3,6-bis(chloromethyl)benzene

Product 1

HCID 20571321HCID 20571321, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a six-liter flask equipped with stirrer, reflux condenser and thermometer, 608.6 L g (4 moles) of 4-hydroxybenzoic acid methyl ester was suspended in 3.5 liters of methyl glycol, and by the addition of 160 g (4 moles ) of sodium hydroxide in 160 ml of water was transformed to a solution of the phenolate. Then, at about 35°-40° C., with stirring, 981.3 g (2 moles) of 1,4-bis-(chloromethyl)-2,3,5,6-tetrabromobenzene was put in, and the reaction mixture was raised steadily to the boiling temperature, with stirring. After an internal temperature of about 90° C. was reached, reaction started, with the formation of a colorless, voluminous precipitate. The reaction mixture, after becoming increasingly thick, became thinner again at the boiling temperature. It was refluxed for 1.5 hours, then cooled down to room temperature; the precipitate was suction filtered and washed free of sodium chloride with water, and dried.

Workup

  1. customIn a six-liter flask equipped with stirrer
  2. temperaturereflux condenser
  3. temperaturewas raised steadily to the boiling temperature
  4. stirringwith stirring
  5. customAfter an internal temperature of about 90° C.
  6. customreaction
  7. temperatureThe reaction mixture, after becoming increasingly thick
  8. temperatureIt was refluxed for 1.5 hours
  9. filtrationfiltered
  10. washwashed free of sodium chloride with water
  11. customdried

Sources & evidence

ORD record
ord-d7f5e8f952bd42f3b1a9d0b7e1167fc1
Source dataset
uspto-grants-1979_05
Patent number
US04152511

Reaction notes

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