Hydrochloric Acid → HCID 20150417, compound

HRID 568732Notes

Reaction equation

HRID 568732 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5]1([CH3:20])[CH2:10][CH2:9][C:8]2[C:11]([CH3:19])=[C:12]([O:17][CH3:18])[C:13]([CH3:16])=[C:14]([CH3:15])[C:7]=2[O:6]1.[C:21]1([CH3:31])[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1.Cl>N1C=CC=CC=1>[CH3:18][O:17][C:12]1[C:13]([CH3:16])=[C:14]([CH3:15])[C:7]2[O:6][C:5]([CH2:4][CH2:3][CH2:2][O:1][S:27]([C:24]3[CH:25]=[CH:26][C:21]([CH3:31])=[CH:22][CH:23]=3)(=[O:29])=[O:28])([CH3:20])[CH2:10][CH2:9][C:8]=2[C:11]=1[CH3:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 20150415HCID 20150415, compound

Product 1

HCID 20150417HCID 20150417, compoundYield 48.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

The crude 3,4-dihydro-2-(3-hydroxypropyl)-6-methoxy-2,5,7,8-tetramethyl-2H-benzopyran (5.0 g) obtained in the above manner was dissolved in 50 ml of pyridine and the solution was cooled to 0° C. To the solution was added slowly 3.9 g of p-toluenesulfonyl chloride with vigorous stirring. After stirring at 0° C. for 1 hour, the reaction mixture was poured into 100 ml of dilute hydrochloric acid and extracted with diethyl ether. The ether layer was washed with water and then with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and filtered. Low-boiling substances were distilled off from the filtrate under reduced pressure. The residue was purified by silica gel column chromatography to give 3.8 g of 3,4-dihydro-6-methoxy-2-[3-(p-toluenesulfonyloxy)propyl]-2,5,7,8-tetramethyl-2H-benzopyran.

Workup

  1. extractionextracted with diethyl ether
  2. washThe ether layer was washed with water
  3. dry with materialwith a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. distillationLow-boiling substances were distilled off from the filtrate under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c6ee6c9596384c5489265481ca741481
Source dataset
uspto-grants-1988_03
Patent number
US04728650

Reaction notes

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