Potassium Carbonate → 4-[N-methyl-N-(11-hydroxyundecyl)-amino]-benzaldehyde

HRID 1590536Notes

Reaction equation

HRID 1590536 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][OH:14].C(=O)([O-])[O-].[K+].[K+].F[C:22]1[CH:29]=[CH:28][C:25]([CH:26]=[O:27])=[CH:24][CH:23]=1.[K+].[Br-]>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].CN1C(=O)N(C)CCC1.O>[CH3:1][N:2]([C:22]1[CH:29]=[CH:28][C:25]([CH:26]=[O:27])=[CH:24][CH:23]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][OH:14]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 680234-FluorobenzaldehydeHCID 253877Potassium BromideHCID 1976727411-(Methylamino)undecan-1-ol

Product 1

HCID 197672734-[N-methyl-N-(11-hydroxyundecyl)-amino]-benzaldehyde

Reagents, catalysts & solvents 3

HCID 21218Trioctylmethylammonium chlorideCatalyst3×HCID 962WaterSolventHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent

Conditions

Temperature
95 °C

Procedure

11.6 g of the N-methyl-N-(11-hydroxyundecyl)amine obtained according to Section 1, 8 g of potassium carbonate powder, 7.18 g of 4-fluorobenzaldehyde and 2 drops of the conventional and known phase transfer catalyst Aliquat® 336 (fatty quaternary ammonium chloride) in 50 ml of dimethylpropyleneurea were stirred for 72 hours at 95° C. Aliquat 336 is a commercial product and constitutes methyl-trioctylammonium chloride. It is a mixture of C8 - and C10 -chains, C8 being predominant. It is used as a phase transfer catalyst and liquid ion exchanger. The reaction mixture was then diluted with 700 ml of water and extracted with three times 50 ml of a solvent mixture of ether and ethyl acetate in a volume ratio of 1:1. The combined extracts were washed with three times 50 ml of water and then dried with sodium sulfate and, after the sodium sulfate had been separated off, were evaporated down. The resulting residue was freed from unconverted benzaldehyde by drying at 60° C. under reduced pressure from an oil pump, this procedure being monitored by thin layer chromatography. The dry product was purified by boiling with active carbon in acetone 12.45 g of 4-[N-methyl-N-(11-hydroxyundecyl)]-amino]-benzaldehyde were obtained, whose IR spectrum (KBr pellet) had bands at 3,400, 2,900, 2,850, 1,660, 1,580, 1,520, 1,460, 1,440, 1,380, 1,310, 1,240, 1,160, 1,050 and 820 cm-1.

Workup

  1. extractionextracted with three times 50 ml of a solvent mixture of ether and ethyl acetate in a volume ratio of 1:1
  2. washThe combined extracts were washed with three times 50 ml of water
  3. dry with materialdried with sodium sulfate
  4. customafter the sodium sulfate had been separated off
  5. customwere evaporated down
  6. customby drying at 60° C. under reduced pressure from an oil pump
  7. customThe dry product was purified
  8. customwere obtained

Sources & evidence

ORD record
ord-604b801518c14612ba2a8574de76e5e9
Source dataset
uspto-grants-1993_04
Patent number
US05204178

Reaction notes

Loading…