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

HRID 1646152
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HRID 1646152 반응식
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]
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참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매
HCID 962Water용매

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온도
50 °C

실험 절차

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 3B (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 min. 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 an equivalent of sodium bromide: IR (KBr) 1711, 1628, 1215 cm-1 ; 1H NMR (DMSO D-6)δ3.70 (s, 3 H), 3.77 (s, 2 H), 7.33-7.41 (m, 3 H), 7.48 (s, 1 H), 7.87-7.89 (m, 2 H); 13C NMR (75 MHz, DMSO D-6)δ49.88, 51.93, 127.36, 128.33, 128.91, 129.82, 134.75, 139.06, 168.60.

후처리

  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

출처 및 근거

ORD 기록
ord-ef5c447857db4c40ae1501d0aba34a0c
출처 데이터셋
uspto-grants-1993_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05178877

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