Formaldehyde → HCID 66649528, compound

HRID 1367609Notes

Reaction equation

HRID 1367609 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 (1 mL) 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-466b1bd3451b41f38fb9b9ea1e378134
Source dataset
uspto-grants-2011_02
Patent number
US07893258B2

Reaction notes

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