Sodium Sulfite → (Z)-2-Carbomethoxy-3-phenyl-2-propene-1-sulfonic Acid Sodium Salt

HRID 1197499Notes

Reaction equation

HRID 1197499 reaction equation
Br[CH2:2]/[C:3](/[C:11]([O:13][CH3:14])=[O:12])=[CH:4]\[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[S:15]([O-:18])([O-:17])=[O:16].[Na+:19].[Na+].[Br-].[Na+].[K+].[Br-]>O.CO>[Na+:19].[C:11](/[C:3](=[CH:4]/[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)/[CH2:2][S:15]([O-:18])(=[O:17])=[O:16])([O:13][CH3:14])=[O:12]

Participants

7

Reactant 4

HCID 24437Sodium SulfiteHCID 253877Potassium BromideHCID 253881Sodium BromideHCID 5904127Methyl 2-(bromomethyl)-3-phenylacrylate

Product 1

HCID 88128861(Z)-2-Carbomethoxy-3-phenyl-2-propene-1-sulfonic Acid Sodium Salt

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a 12 L, 3-neck round bottom flask fitted with a mechanical stirrer, thermometer and an addition funnel was added the resultant product from Example 1B (400 g, 1.57 mol) and methanol (4 L). The mixture was warmed to 50° C. and a solution of sodium sulfite (199 g, 1.57 mol) dissolved in water (4 L) was added over 75 min while the internal temperature of the flask was maintained at 50° C. After the addition was complete, the clear solution was allowed to stir at 50° C. for an additional 45 minutes. The reaction mixture in solution was taken to the next step without additional purification. The compound may be isolated by concentration to an amorphous powder, which is contaminated with one equivalent of sodium bromide: IR (KBr) 1711, 1628, 1215 cm-1 ; 1H NMR (DMSO-d6, 300 MHz) δ3.70 (s, 3H), 3.77 (s, 2H), 7.33-7.41 (m, 3H), 7.48 (s, 1H), 7.87-7.89 (m. 2H); 13C NMR (75 MHz, DMSO-d6) δ49.88, 51.93, 127.36, 128.33, 128.91, 129.82, 134.75, 139.06, 168.60.

Workup

  1. customTo a 12 L, 3-neck round bottom flask fitted with a mechanical stirrer
  2. additionwas added over 75 min while the internal temperature of the flask
  3. temperaturewas maintained at 50° C
  4. additionAfter the addition
  5. customThe reaction mixture in solution was taken to the next step without additional purification
  6. customThe compound may be isolated by concentration to an amorphous powder, which

Sources & evidence

ORD record
ord-7b359a286ff4483d87f1970b253ee1db
Source dataset
uspto-grants-1994_01
Patent number
US05275950

Reaction notes

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