Hydrochloric Acid → HCID 10243542, compound

HRID 654674Notes

Reaction equation

HRID 654674 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[C:6]([CH2:13][CH2:14][CH3:15])[CH:7]=[CH:8][CH:9]=2)[C:4]=1[O:16]COC.Cl.O.[C:22](OCC)(=[O:24])C>CC(C)=O>[OH:16][C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][C:6]=2[CH2:13][CH2:14][CH3:15])[C:11]([CH:22]=[O:24])=[CH:12][C:3]=1[O:2][CH3:1]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8857Ethyl AcetateHCID 11777392HCID 11777392, compound

Product 1

HCID 10243542HCID 10243542, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

206 g of 2-methoxy-1-methoxymethoxy-8-propylnaphthalene was dissolved in 1160 ml of acetone and cooled to 0° C. Diluted hydrochloric acid (concentrated hydrochloric acid 84 ml/water 206 ml) was added to the solution in 15 minutes, which was returned to room temperature at which the reaction was effected at 20° C. for 5 hours, followed by addition of water and extraction with ethyl acetate. The resultant organic phase was washed with a saturated saline solution to neutrality, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. 173 g of the resultant brown oily substance was dissolved in 1350 g of dichloromethane without purification and cooled down to 0° C. 176.3 ml of titanium tetrachloride was dropped in the solution at 5° C. or below, to which 114.3 ml of dichloromethyl methyl ether was added at 5° C. or below at which the reaction was carried out for 10 minutes. The reaction solution was slowly added to iced water and extracted with ethyl acetate. The resultant organic phase was washed with a saturated sodium hydrogencarbonate aqueous solution and a saturated saline solution in this order and dried with anhydrous magnesium sulfate, and was concentrated under reduced pressure. The resultant crystals were washed with a 30% isopropyl ether/hexane solution to obtain 103 g of the captioned compound as yellowish brown crystals.

Workup

  1. customwas returned to room temperature at which
  2. washThe resultant organic phase was washed with a saturated saline solution to neutrality
  3. dry with materialdried with anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. dissolution173 g of the resultant brown oily substance was dissolved in 1350 g of dichloromethane without purification
  6. temperaturecooled down to 0° C
  7. addition176.3 ml of titanium tetrachloride was dropped in the solution at 5° C. or below, to which 114.3 ml of dichloromethyl methyl ether
  8. additionwas added at 5° C. or below at which the reaction
  9. waitwas carried out for 10 minutes
  10. additionThe reaction solution was slowly added to iced water
  11. extractionextracted with ethyl acetate
  12. washThe resultant organic phase was washed with a saturated sodium hydrogencarbonate aqueous solution
  13. dry with materiala saturated saline solution in this order and dried with anhydrous magnesium sulfate
  14. concentrationwas concentrated under reduced pressure
  15. washThe resultant crystals were washed with a 30% isopropyl ether/hexane solution

Sources & evidence

ORD record
ord-979ca99f3b874362894424c91b193098
Source dataset
uspto-grants-1992_07
Patent number
US05134111

Reaction notes

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