Water → HCID 10330411, compound

HRID 654689Notes

Reaction equation

HRID 654689 reaction equation
[CH2:1]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[C:11]([OH:13])=[CH:10][CH:9]=[CH:8]2)[CH3:2].[CH3:14][O:15]C(Cl)Cl.O>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[CH2:1]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[C:11]([OH:13])=[CH:10][CH:9]=[C:8]2[CH:14]=[O:15])[CH3:2]

Participants

6

Reactant 3

HCID 962WaterHCID 21004Methane, dichloromethoxy-HCID 10397246HCID 10397246, compound

Product 1

HCID 10330411HCID 10330411, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 24193Titanium TetrachlorideSolvent

Procedure

24.0 g of 8-ethyl-1-naphthol was dissolved in 200 ml of dichloromethane, in which 30.6 ml of titanium tetrachloride was gradually dropped under ice-cooling conditions. Thereafter, 20.3 ml of dichloromethyl methyl ether was gradually dropped under ice-cooling condition. After agitation for 10 minutes, 50 ml of water was gradually dropped under ice-cooling conditions. The reaction solution was extracted with ethyl acetate and the organic phase was washed with water. After drying with anhydrous magnesium sulfate, the solvent was distilled off and the resultant crystals were washed with a mixed solvent of chloroform and isopropyl ether (1:1) to obtain 15.9 g of the captioned compound as yellowish brown crystals.

Workup

  1. additionwas gradually dropped under ice-
  2. temperaturecooling conditions
  3. temperaturecooling condition
  4. temperaturecooling conditions
  5. extractionThe reaction solution was extracted with ethyl acetate
  6. washthe organic phase was washed with water
  7. dry with materialAfter drying with anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off
  9. washthe resultant crystals were washed with a mixed solvent of chloroform and isopropyl ether (1:1)

Sources & evidence

ORD record
ord-97dfe945979c41d583cd34d507af5f00
Source dataset
uspto-grants-1992_07
Patent number
US05134111

Reaction notes

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