Methanol → 1-Octyl-2-pyrrolidone

HRID 1721013Notes

Reaction equation

HRID 1721013 reaction equation
C[O-].[K+].CO.CO.[NH:8]1[CH2:12][CH2:11][CH2:10][C:9]1=[O:13].[CH2:14](Cl)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]>COCCOCCOC>[CH2:14]([N:8]1[CH2:12][CH2:11][CH2:10][C:9]1=[O:13])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

6

Reactant 4

HCID 887MethanolHCID 81421-ChlorooctaneHCID 120252-PyrrolidoneHCID 87293205HCID 87293205, compound

Product 1

HCID 30338711-Octyl-2-pyrrolidone

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Procedure

230 g of a 31.98 wt. % strength potassium methoxide-methanol solution (1.05 mol) is added dropwise at about 155° C., while distilling methanol to a solution of 85.2 g of 2-pyrrolidone (butyrolactam, 1.0 mol) in 500 ml of diethylene glycol dimethyl ether. For complete removal of all the methanol, the clear solution is evacuated for a short period until reaching 500 mbar. 156 g of n-octyl chloride (1.05 mol) is then metered in likewise at 155° C. over a period of 20 minutes, and the reaction is brought to completion over a period of another 6 hours.

Workup

  1. customFor complete removal of all the methanol
  2. customthe clear solution is evacuated for a short period
  3. customlikewise at 155° C.
  4. customof 20 minutes

Sources & evidence

ORD record
ord-85e354af65d34753867af94309aa3502
Source dataset
uspto-grants-1996_04
Patent number
US05508396

Reaction notes

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