Methane, dichloromethoxy- → HCID 19767560, compound

HRID 1590555Notes

Reaction equation

HRID 1590555 reaction equation
[C:1]([C:5]1[CH:14]=[CH:13][C:12]2[CH2:11][CH2:10][CH2:9][CH2:8][C:7]=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[CH2:11][CH2:10][CH2:9][CH2:8][C:7]=2[C:6]=1[OH:15])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 21004Methane, dichloromethoxy-HCID 197675552-tert-Butyl-5,6,7,8-tetrahydronaphthalen-1-ol

Product 1

HCID 19767560HCID 19767560, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Stannic chloride (36.71 g, 0.141 mole) was added to a solution of 2-tert-butyl-5,6,7,8-tetrahydro-1-naphthol (16.0 g, 0.0783 mole) in dry dichloromethane (150 ml) at -10°. To the stirred solution was added 1,1-dichloromethyl methyl ether (13.45 g, 0.118 mole) dropwise at 0°. After 10 minutes, the reaction mixture was treated with ice-water and extracted with ethyl acetate (2×200 ml). The organic extract washed with aqueous saturated sodium chloride and dried over magnesium sulphate. The solvents were removed in vacuo and the solid residue was triturated with n-pentane:diethyl ether (4:1) mixture to give a grey white crystalline solid which was filtered off and air-dried to yield 10.15 g (55.7%), m.p. 193°-94°.

Workup

  1. extractionextracted with ethyl acetate (2×200 ml)
  2. extractionThe organic extract
  3. washwashed with aqueous saturated sodium chloride
  4. dry with materialdried over magnesium sulphate
  5. customThe solvents were removed in vacuo
  6. customthe solid residue was triturated with n-pentane:diethyl ether (4:1) mixture
  7. customto give a grey white crystalline solid which
  8. filtrationwas filtered off
  9. customair-dried
  10. customto yield 10.15 g (55.7%), m.p. 193°-94°

Sources & evidence

ORD record
ord-e9105b7db6c64109b807cfa72d5f6aba
Source dataset
uspto-grants-1993_04
Patent number
US05204336

Reaction notes

Loading…