Chloromethyl Methyl Ether → HCID 21402946, compound

HRID 1287630Notes

Reaction equation

HRID 1287630 reaction equation
[Mg].[CH3:2][O:3][CH2:4]Cl.[CH:6]1[C:16]2[CH2:15][CH2:14][C:13]3[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=3[C:11](=[O:21])[C:10]=2[CH:9]=[CH:8][CH:7]=1>O1CCCC1>[CH3:2][O:3][CH2:4][C:11]1([OH:21])[C:12]2[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=2[CH2:14][CH2:15][C:16]2[CH:6]=[CH:7][CH:8]=[CH:9][C:10]1=2

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 14589DibenzosuberoneHCID 5462224Magnesium

Product 1

HCID 21402946HCID 21402946, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of chloromethyl methyl ether (40.2 g, 0.5 mole, freshly distilled) in dry tetrahydrofuran (80 ml) is prepared, and about 5 ml of that solution are added to a stirred mixture of magnesium turnings (12.0 g, 0.5 g - atom) and mercuric chloride (500 mg) in tetrahydrofuran (20 ml) until an exothermic reaction ensues. The flask is cooled to 0°± 10° and the remainder of the chloromethyl methyl ether solution is added dropwise with thorough agitation. After completion of addition a solution of 10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one (56.1 g 0.25 mole) in tetrahydrofuran is added dropwise. The reaction mixture is stirred overnight at room temperature and the complex is hydrolyzed with ice-cold ammonium chloride solution. The aqueous layer is extracted with ether (3 × 100 ml) and the combined extracts are washed with sodium chloride solution, dried and evaporated under reduced pressure to give 10,11-dihydro-5-methoxymethyl-5H-dibenzo[a,d]cyclohepten-5-ol as an oil with b.p. 143°- 144° C/0.05 mm, γmaxfilm : 3500 cm-1, 2820 cm-1.

Workup

  1. distillationA solution of chloromethyl methyl ether (40.2 g, 0.5 mole, freshly distilled) in dry tetrahydrofuran (80 ml)
  2. customis prepared
  3. temperatureThe flask is cooled to 0°± 10°
  4. additionis added dropwise
  5. extractionThe aqueous layer is extracted with ether (3 × 100 ml)
  6. washthe combined extracts are washed with sodium chloride solution
  7. customdried
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-9c87685ce7b44373ad07ea923299251c
Source dataset
uspto-grants-1976_10
Patent number
US03985751

Reaction notes

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