Chloromethyl Methyl Ether → HCID 22347859, compound

HRID 976342Notes

Reaction equation

HRID 976342 reaction equation
[CH3:1][C:2]1([CH3:15])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([OH:14])[CH:5]=[CH:4][C:3]1=2.[H-].[Na+].[CH3:18][O:19][CH2:20]Cl.C(=O)([O-])O.[Na+]>CN(C)C=O>[CH3:18][O:19][CH2:20][O:14][C:6]1[CH:5]=[CH:4][C:3]2[C:2]([CH3:15])([CH3:1])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]=2[CH:7]=1

Participants

6

Reactant 4

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 2687865,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-olHCID 516892Sodium Bicarbonate

Product 1

HCID 22347859HCID 22347859, compoundYield 106.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

10 ml of a solution of 4.0 g of 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthol in N,N-dimethylformamide was dropwise added to 70 ml of a suspension of 1.01 g of sodium hydride (604 solution in oil) in anhydrous N,N-dimethylformamide at 0° C. The obtained mixture was stirred at room temperature for one hour and cooled to 0° C., followed by the addition thereto of 5 ml of a solution of 2.36 g of chloromethyl methyl ether in N,N-dimethylformamide. The temperature of the mixture was gradually raised to room temperature (in 10 minutes). The resulting mixture was further stirred for one hour, followed by the addition thereto of 30 ml of a saturated aqueous solution of sodium hydrogencarbonate. The obtained mixture was extracted with ethyl acetate. The organic phase was washed with a saturated aqueous solution of common salt, dried over anhydrous magnesium sulfate and distilled to remove the solvent. The residue was purified by silica gel chromatography (developer: 5% ethyl acetate/n-hexane) to give 5.2 g of the title compound as a colorless oil. 1H-NMR (400 MHz, CDCl3) δ(ppm); 1.26(s, 6H), 1.29(s, 6H), 1.70(s, 4H), 3.50(s, 3H), 5.18(s, 2H), 6.87(dd, J=8.4, 2.4 Hz, 1H), 6.97(d, J=2.4 Hz, 1H), 7.23(d, J=8.4 Hz, 1H)

Workup

  1. temperaturecooled to 0° C.
  2. additionfollowed by the addition
  3. temperatureThe temperature of the mixture was gradually raised to room temperature (in 10 minutes)
  4. stirringThe resulting mixture was further stirred for one hour
  5. additionfollowed by the addition
  6. extractionThe obtained mixture was extracted with ethyl acetate
  7. washThe organic phase was washed with a saturated aqueous solution of common salt
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationdistilled
  10. customto remove the solvent
  11. customThe residue was purified by silica gel chromatography (developer: 5% ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-ee19ea15c314446cbc3c0fb8dd1b1309
Source dataset
uspto-grants-1997_03
Patent number
US05612356

Reaction notes

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