Hydrochloric Acid → HCID 20150421, compound

HRID 568731Notes

Reaction equation

HRID 568731 reaction equation
[OH-].[K+].[OH:3][C:4]1[C:5]([CH3:22])=[C:6]([CH3:21])[C:7]2[O:12][C:11]([CH2:14][CH2:15][C:16]([OH:18])=O)([CH3:13])[CH2:10][CH2:9][C:8]=2[C:19]=1[CH3:20].S([O:28][CH3:29])(OC)(=O)=O.Cl.[CH3:31]N(C)C=O>C(O)C>[CH3:31][O:3][C:4]1[C:5]([CH3:22])=[C:6]([CH3:21])[C:7]2[O:12][C:11]([CH2:14][CH2:15][C:16]([O:28][CH3:29])=[O:18])([CH3:13])[CH2:10][CH2:9][C:8]=2[C:19]=1[CH3:20]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 6497Dimethyl SulfateHCID 14797Potassium HydroxideHCID 99435424072-32-6

Product 1

HCID 20150421HCID 20150421, compoundYield 53.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

An aqueous solution of potassium hydroxide (7.1 g in 10 ml of water) was added dropwise to a solution composed of 10 g (0.036 mol) of 3-(3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-benzopyran-2-yl)propionic acid and 200 ml of ethanol in a nitrogen atmosphere and the mixture was stirred at room temperature for 30 minutes. The ethanol was distilled off from the reaction mixture under reduced pressure, toluene was added to the residue, and dehydration was effected azeotropically under reduced pressure. To the residue thus obtained, 200 ml of N,N-dimethylformamide was added for dissolution of the residue. To the solution was added dropwise, with vigorous stirring, 4.53 g (3.4 ml) of dimethyl sulfate while maintaining the solution at a temperature of room temperature to 50° C. After the addition, the reaction was conducted at 50° C. for 5 hours. After cooling to room temperature, the reaction mixture was poured into dilute hydrochloric acid and extracted with diethyl ether. The extract was washed with water and then with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and then filtered. Low-boiling substances were distilled off from the filtrate under reduced pressure and the residue was purified by silica gel column chromatography to give 5.9 g (53.6% yield) of methyl 3-(3,4-dihydro-6-methoxy-2,5,7,8-tetramethyl-2H-benzopyran-2-yl)propionate

Workup

  1. distillationThe ethanol was distilled off from the reaction mixture under reduced pressure, toluene
  2. additionwas added to the residue, and dehydration
  3. customTo the residue thus obtained
  4. temperaturewhile maintaining the solution at a temperature of room temperature to 50° C
  5. additionAfter the addition
  6. waitthe reaction was conducted at 50° C. for 5 hours
  7. temperatureAfter cooling to room temperature
  8. extractionextracted with diethyl ether
  9. washThe extract was washed with water
  10. dry with materialwith a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate
  11. filtrationfiltered
  12. distillationLow-boiling substances were distilled off from the filtrate under reduced pressure
  13. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e992e99d331a4bf89afaeafa57d17f51
Source dataset
uspto-grants-1988_03
Patent number
US04728650

Reaction notes

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