Hydrochloric Acid → 4-Methoxy-3-tricyclo[3.3.1.13,7]dec-1-ylbenzaldehyde

HRID 2293633Notes

Reaction equation

HRID 2293633 reaction equation
[C:1]12([C:11]3[CH:16]=[C:15](Br)[CH:14]=[CH:13][C:12]=3[O:18][CH3:19])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[Mg].II.CN([CH:26]=[O:27])C.Cl>C1COCC1.ClCCl>[C:1]12([C:11]3[CH:16]=[C:15]([CH:14]=[CH:13][C:12]=3[O:18][CH3:19])[CH:26]=[O:27])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 807IodineHCID 6228DimethylformamideHCID 32850241-(5-Bromo-2-methoxyphenyl)adamantaneHCID 5462224Magnesium

Product 1

HCID 540295304-Methoxy-3-tricyclo[3.3.1.13,7]dec-1-ylbenzaldehyde

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

11.09 g (37 mmoles) of 2-(1-adamantyl)-4-bromo anisole dissolved in 85 ml of THF are slowly added to 1 g of magnesium and an iodine crystal. At the beginning of the addition, the reaction mixture is heated until the reaction begins, then the remainder of the solution is added in a manner to maintain a regular reflux. This reaction mixture is heated at reflux for 30 minutes after the end of the addition at which point 2.70 g (37 mmoles) of dry DMF are added. The reaction mixture is then stirred for 30 minutes without heating and then poured into 300 ml of mixture of 2N aqueous HCl and dichloromethane.

Workup

  1. additionAt the beginning of the addition
  2. temperaturethe reaction mixture is heated until the reaction
  3. additionthe remainder of the solution is added in a manner
  4. temperatureto maintain a regular reflux
  5. temperatureThis reaction mixture is heated
  6. temperatureat reflux for 30 minutes
  7. additionare added
  8. temperaturewithout heating

Sources & evidence

ORD record
ord-f66d177cd4d74afc9005174c9c64eb8d
Source dataset
uspto-grants-1997_11
Patent number
US05686586

Reaction notes

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