Chloromethyl Methyl Ether → HCID 21402946, compound

HRID 972956Notes

Reaction equation

HRID 972956 reaction equation
[Mg].[CH3:2][O:3][CH2:4]Cl.[CH2:6]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:14](=[O:15])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1>O1CCCC1>[CH3:2][O:3][CH2:4][C:14]1([OH:15])[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=2[CH2:6][CH2:7][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:13]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,b]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-b0bdbfa3f6b84d959443ae69c1ae2768
Source dataset
uspto-grants-1977_10
Patent number
US04054569

Reaction notes

Loading…