Sulfuric Acid → Methyl 6-hydroxy-2,5,7,8-tetramethylchroman-2-acetate

HRID 1978354Notes

Reaction equation

HRID 1978354 reaction equation
[OH:1][C:2]1[C:3]([CH3:19])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([CH3:18])([CH2:14][C:15]([OH:17])=[O:16])[CH2:6][CH2:5]2.S(=O)(=O)(O)O.[C:25](=O)([O-])O.[Na+]>CO>[OH:1][C:2]1[C:3]([CH3:19])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([CH3:18])([CH2:14][C:15]([O:17][CH3:25])=[O:16])[CH2:6][CH2:5]2

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 55926-Hydroxy-2,5,7,8-tetramethylchroman-2-acetic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 13909413Methyl 6-hydroxy-2,5,7,8-tetramethylchroman-2-acetate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 10.0 g (37.83 mM) of 6-hydroxy-2,5,7,8-tetramethylchroman-2-acetic acid in methanol (50 ml) was added 0.5 ml (6 mM) of concentrated sulfuric acid at room temperature and the mixture was stirred for 3 days. To this reaction mixture was added a saturated aqueous solution of sodium hydrogen carbonate at 0° C. until the pH had been brought to 5-7 and the solvent was then distilled off under reduced pressure. The residue was diluted with water and extracted with diethyl ether. The organic layer was washed with saturated aqueous solution of sodium chloride and dried over MgSO4. The solvent was then distilled off under reduced pressure to provide the title compound as tan-colored oil.

Workup

  1. distillationthe solvent was then distilled off under reduced pressure
  2. additionThe residue was diluted with water
  3. extractionextracted with diethyl ether
  4. washThe organic layer was washed with saturated aqueous solution of sodium chloride
  5. dry with materialdried over MgSO4
  6. distillationThe solvent was then distilled off under reduced pressure

Sources & evidence

ORD record
ord-9a1133b3d50d4f2080333dbcb6defd30
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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