Methylparaben → HCID 23712208, compound

HRID 258803Notes

Reaction equation

HRID 258803 reaction equation
C[O-].[Na+:3].C(C1C=CC(O)=CC=1)(OC)=O.C1CS(=O)C1.[C:20]([C:24]1[CH:37]=[CH:36][C:27]([O:28][CH2:29][CH2:30][CH2:31][S:32]([O-:35])(=[O:34])=[O:33])=[CH:26][CH:25]=1)([O:22][CH3:23])=[O:21].C([P+](CCCC)(CCCC)CCCC)CCC>CO>[C:20]([C:24]1[CH:37]=[CH:36][C:27]([O:28][CH2:29][CH2:30][CH2:31][S:32]([O-:35])(=[O:33])=[O:34])=[CH:26][CH:25]=1)([O:22][CH3:23])=[O:21].[Na+:3]

Participants

6

Reactant 4

HCID 7456MethylparabenHCID 25747Thietane, 1-oxide (9CI)HCID 10942334Sodium MethoxideHCID 21424533HCID 21424533, compound

Product 1

HCID 23712208HCID 23712208, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium 3-(4-carbomethoxyphenoxy)propanesulfonate is prepared by adding sodium methoxide (54 grams) to 4-carbomethoxyphenol (152 grams) dissolved in 600 ml. of methanol followed by addition of propane sulfone (122 grams). After 2 hours of reflux, the crystals formed are filtered (186 grams) and added to tetra-n-butylphosphonium chloride (185 grams) in 400 ml. of water at 40° C. to prepare tetra-n-butylphosphonium 3-(4-carbomethoxyphenoxy)propanesulfonate. To remove this phosphonium salt from water, 70-ml. of chloroform is shaken with 70-ml. of the water solution and then separated from the water. This chloroform layer is then combined with the chloroform layer from a repeat of this procedure with 100-ml. of chloroform and a 100-ml. portion of the water solution. Evaporation of the combined chloroform extracts yields 98 g. of Salt E.

Workup

  1. dissolutiondissolved in 600 ml
  2. temperatureAfter 2 hours of reflux
  3. customthe crystals formed
  4. filtrationare filtered (186 grams)
  5. additionadded to tetra-n-butylphosphonium chloride (185 grams) in 400 ml
  6. customof water at 40° C. to prepare tetra-n-butylphosphonium 3-(4-carbomethoxyphenoxy)propanesulfonate
  7. customTo remove this phosphonium salt from water, 70-ml
  8. customof the water solution and then separated from the water
  9. customEvaporation of the combined chloroform
  10. customextracts yields 98 g

Sources & evidence

ORD record
ord-bf49107bc2e54d779cb457bb52a157bd
Source dataset
uspto-grants-1977_07
Patent number
US04035346

Reaction notes

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