Water → HCID 9815673, compound

HRID 1760135Notes

Reaction equation

HRID 1760135 reaction equation
[CH2:1]([O:3][CH:4]1[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][C:8]([OH:14])=[CH:9][CH:10]=2)[O:5]1)[CH3:2].S(OC)(O[CH3:19])(=O)=O.[OH-].[Na+].O>CO>[CH2:1]([O:3][CH:4]1[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:19])=[CH:9][CH:10]=2)[O:5]1)[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 14577961HCID 14577961, compound

Product 1

HCID 9815673HCID 9815673, compoundYield 94.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The above-obtained 2-ethoxy-7-hydroxychroman (10.9 g) was dissolved in 60 ml of methanol, and 10.6 g of dimethyl sulfate and 13.5 g of a 25% sodium hydroxide aqueous solution were added thereto at room temperature. The mixture was stirred at this temperature for 1 hour. After 30 ml of water was added thereto, the methanol was removed by distillation in vacuo, and the residue was extracted twice with 50 ml of toluene. The toluene layer was washed with water, and the toluene was removed by distillation in vacuo. The resulting residue was purified by distillation to obtain 11.0 g of a desired colorless liquid (yield 94%).

Workup

  1. customat room temperature
  2. customthe methanol was removed by distillation in vacuo
  3. extractionthe residue was extracted twice with 50 ml of toluene
  4. washThe toluene layer was washed with water
  5. customthe toluene was removed by distillation in vacuo
  6. distillationThe resulting residue was purified by distillation

Sources & evidence

ORD record
ord-e4ff53cd77d84fb89778bf397d2d69f2
Source dataset
uspto-grants-2005_01
Patent number
US06841183B2

Reaction notes

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