Hydrochloric Acid → HCID 86668197, compound

HRID 243806Notes

Reaction equation

HRID 243806 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([CH3:15])[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1.[CH3:16][O:17]C(Cl)Cl.Cl>ClCCl.C(OCC)(=O)C.[Ti](Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2([CH3:15])[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[CH:7][C:8]=1[CH:16]=[O:17]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 21004Methane, dichloromethoxy-HCID 68107165HCID 68107165, compound

Product 1

HCID 86668197HCID 86668197, compoundYield 122.3%

Reagents, catalysts & solvents 3

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-(4-methoxyphenyl)-4-methyltetrahydro-2H-pyran (0.518 g, 2.51 mmol) in dichloromethane (12.0 mL) was cooled to −15° C., and titanium tetrachloride (1.22 mL, 11.0 mmol) was added dropwise thereto. After stirring the mixture for 20 minutes, dichloromethyl methyl ether (0.336 mL, 3.77 mmol) was added dropwise thereto. After stirring the mixture for 1 hour, 1 mol/L hydrochloric acid was added to stop the reaction. The reaction solution was diluted with ethyl acetate, and the organic layer was washed with water and then with saturated brine, dried over anhydrous sodium sulfate and filtered. The solvent was then evaporated under reduced pressure to obtain 0.719 g of the crude product containing the captioned compound.

Workup

  1. stirringAfter stirring the mixture for 1 hour
  2. customthe reaction
  3. washthe organic layer was washed with water
  4. dry with materialwith saturated brine, dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customThe solvent was then evaporated under reduced pressure

Sources & evidence

ORD record
ord-29b481cd8c8f4b708e0ca18d04b3c0cd
Source dataset
uspto-grants-2014_02
Patent number
US08653304B2

Reaction notes

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