Formaldehyde → HCID 66649528, compound

HRID 419781Notes

Reaction equation

HRID 419781 reaction equation
[CH2:1]=O.[OH:3][CH2:4][CH2:5][NH:6][CH2:7][CH2:8][O:9][CH2:10][CH:11]([OH:22])[CH2:12][CH2:13][CH2:14][CH:15]([CH2:19][CH2:20][CH3:21])[CH2:16][CH2:17][CH3:18]>C1(C)C=CC=CC=1.C(O)(C)C>[O:3]1[CH2:4][CH2:5][N:6]([CH2:7][CH2:8][O:9][CH2:10][CH:11]([OH:22])[CH2:12][CH2:13][CH2:14][CH:15]([CH2:19][CH2:20][CH3:21])[CH2:16][CH2:17][CH3:18])[CH2:1]1

Participants

5

Reactant 2

HCID 712FormaldehydeHCID 25023068HCID 25023068, compound

Product 1

HCID 66649528HCID 66649528, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3776IsopropanolSolvent

Procedure

To a 10 mL flask containing paraformaldehyde (52 mg, 1,73 mmol, 1 eq.) in toluene (1 mL), was added 1-[2-(2-hydroxy-ethylamino)-ethoxy]-6-propyl-nonan-2-ol (500 mg 1,73 mmol) diluted with isopropanol (1mL) before heating to reflux with a Dean-Stark trap for 17 h. The reaction was cooled to room temperature and, after evaporation, 520 mg of a mixture of products was obtained with the title compound as the major component (100% crude yield). 1H NMR (CDCl3, 400 MHz) d?(ppm); 4,33 (s, 2H); 3,78 (t, J=6,8 Hz, 2H); 3,83-3,74 (m, H); 3,70-3,57 (m, 2H); 3,55 (dd, J=2,7 Hz, J=10,0 Hz, H); 3,29 (dd, J=8,2 Hz, J=10,0 Hz, H); 3,02 (t, J=6,8 Hz, 2H); 2,81-2,74 (m, 2H); 1,50-1,12 (m, 15H); 0,87 (t, J=7,0 Hz, 6H′). 13C NMR (CDCl3, 129,9 MHz) d?(ppm): 87,0; 76,0; 70,5; 70,3; 63,3; 54,3; 52,7; 36,9; 36,0 (2C); 33,7; 33,5; 22,7; 19,8 (2C); 14,5 (2C)

Workup

  1. temperaturebefore heating
  2. temperatureto reflux with a Dean-Stark trap for 17 h
  3. customafter evaporation, 520 mg of a mixture of products

Sources & evidence

ORD record
ord-7d79de5a646d4282ae8f57b78d380b0f
Source dataset
uspto-grants-2012_01
Patent number
US08093398B2

Reaction notes

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