Methane, dichloromethoxy- → HCID 19767558, compound

HRID 1590554Notes

Reaction equation

HRID 1590554 reaction equation
[C:1]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2].[CH3:16][O:17]C(Cl)Cl>ClCCl>[C:1]([C:5]1[CH:14]=[C:13]([CH:16]=[O:17])[C:12]2[C:7]([C:6]=1[OH:15])=[CH:8][CH:9]=[CH:10][CH:11]=2)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 21004Methane, dichloromethoxy-HCID 10910545HCID 10910545, compound

Product 1

HCID 19767558HCID 19767558, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 0° solution of 2-t-butyl-1-naphthol (7.6 g, 0.038 mole) in 50 ml of dry dichloromethane was added anhydrous stannic chloride (19.77 g, 0.076 mole). The resulting reaction mixture was stirred at 0° during the dropwise addition of 1,1-dichloromethyl methyl ether (7.75 g, 0.068 mole). The mixture was stirred for 10 minutes at 0° then poured into ice/water. The resulting mixture was extracted with diethyl ether (3×200 ml). The ethereal extracts were washed with water until the aqueous washes had a neutral pH and then dried over magnesium sulphate. The solvent was removed in vacuo to give a solid residue which was triturated with a mixture of diethyl ether: n-pentane (1:4) to give 3.8 g (44% yield) of a crystalline solid, m.p. 195°-196°.

Workup

  1. customThe resulting reaction mixture
  2. extractionThe resulting mixture was extracted with diethyl ether (3×200 ml)
  3. washThe ethereal extracts were washed with water until the aqueous washes
  4. dry with materialdried over magnesium sulphate
  5. customThe solvent was removed in vacuo
  6. customto give a solid residue which
  7. customwas triturated with a mixture of diethyl ether: n-pentane (1:4)

Sources & evidence

ORD record
ord-e2f358ee46dd447984c2e8aca57288ae
Source dataset
uspto-grants-1993_04
Patent number
US05204336

Reaction notes

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