m-Xylyl chloride → HCID 23452549, compound

HRID 1278055Notes

Reaction equation

HRID 1278055 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5]Cl.[Mg].C(O[C:14]1(OCC)[CH2:18][CH2:17][CH2:16][N:15]1[CH3:19])C.[Cl-].[NH4+]>C(OCC)C>[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][CH:14]1[CH2:18][CH2:17][CH2:16][N:15]1[CH3:19]

Participants

6

Reactant 4

HCID 12102m-Xylyl chlorideHCID 25517Ammonium ChlorideHCID 2973082,2-Diethoxy-1-methylpyrrolidineHCID 5462224Magnesium

Product 1

HCID 23452549HCID 23452549, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Prepare a Grignard solution from 103 g of 3-methylbenzyl chloride and 8 g of magnesium in 400 ml of diethyl ether. With stirring and boiling under reflux, add a solution of 126.9 g of 2,2-diethoxy-1-methylpyrrolidine dropwise to the Grignard solution. Keep the thus-prepared mixture at the boil for a further 1 hour before adding 130 ml of saturated ammonium chloride solution dropwise thereto. Then filter off the magnesium salts and dry the filtrate over sodium sulfate. Free the residue (31 g) from ether and then hydrogenate it with Raney nickel/hydrogen. Distil the hydrogenated product twice under a vacuum to obtain 16.2 g (13% of theory) of the title compound (b.p. 56° to 0.001 mm of Hg).

Workup

  1. temperatureunder reflux
  2. customfor a further 1 hour
  3. filtrationThen filter off the magnesium salts
  4. dry with materialdry the filtrate over sodium sulfate
  5. customDistil the hydrogenated product twice under a vacuum

Sources & evidence

ORD record
ord-5df62b38c6ea47eb900f88171ea5122a
Source dataset
uspto-grants-1981_07
Patent number
US04279918

Reaction notes

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