Sodium Bicarbonate → HCID 130039219, compound

HRID 726176Notes

Reaction equation

HRID 726176 reaction equation
[C:1]([C:5]1[CH:16]=[CH:15][CH:14]=[CH:13][C:6]=1[S:7][CH2:8][CH2:9][C:10]([OH:12])=O)([O:3][CH3:4])=[O:2].C(=O)([O-])O.[Na+]>>[CH3:4][O:3][C:1]([C:5]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:6]=1[S:7][CH2:8][CH2:9][C:10]2=[O:12])=[O:2]

Participants

3

Reactant 2

HCID 516892Sodium BicarbonateHCID 131720390HCID 131720390, compound

Product 1

HCID 130039219HCID 130039219, compoundYield 43.2%

Procedure

β(2-Carbomethoxythiophenoxy)propionic acid (6.00 g, 0.025 mol) (I. W. Still and M. J. Thomas J. Org. Chem 1968, 2733) was added slowly to ice cooled conc. sulphuric acid (75 ml) with stirring. After 21 h, the reaction mixture was poured into ice water and then made alkaline using solid sodium hydrogen carbonate. The resultant suspension was then extracted with CH2Cl2 (3x). The combined organic layers were then dried (Na2SO4), and evaporated under reduced pressure to give an orange oil which was dried in vacuo and crystallised on standing to give methylthiochroman-4-one-8-carboxylate (2.40 g, 43%)

Workup

  1. extractionThe resultant suspension was then extracted with CH2Cl2 (3x)
  2. dry with materialThe combined organic layers were then dried (Na2SO4)
  3. customevaporated under reduced pressure
  4. customto give an orange oil which
  5. customwas dried in vacuo
  6. customcrystallised

Sources & evidence

ORD record
ord-117ded7c0fc7462e97d08fb72c7b7e53
Source dataset
uspto-grants-1998_01
Patent number
US05708174

Reaction notes

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