4-Hydroxybenzaldehyde → HCID 10526636, compound

HRID 273747Notes

Reaction equation

HRID 273747 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1.[CH2:12]([O:19][C:20]1[C:21]([CH3:35])=[C:22]2[C:27](=[C:28]([CH3:31])[C:29]=1[CH3:30])[O:26][C:25]([CH2:33]I)([CH3:32])[CH2:24][CH2:23]2)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CN(C)C=O>[CH2:12]([O:19][C:20]1[C:21]([CH3:35])=[C:22]2[C:27](=[C:28]([CH3:31])[C:29]=1[CH3:30])[O:26][C:25]([CH2:32][O:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1)([CH3:33])[CH2:24][CH2:23]2)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 24758Sodium hydrideHCID 20094300HCID 20094300, compound

Product 1

HCID 10526636HCID 10526636, compoundYield 97.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A mixture of 1.63 g of sodium hydride (as a 55% w/w dispersion in mineral oil) and 20 ml of dimethylformamide was cooled in an atmosphere of nitrogen; to the cooled solution were then added dropwise a mixture of 4.58 g of p-hydroxybenzaldehyde and 30 ml of dimethylformamide, whilst ice-cooling. 10.9 g of 6-benzyloxy-2-iodomethyl-2,5,7,8-tetramethylchroman (prepared as described in Preparation 2) and 50 ml of dimethylformamide were then added to the resulting solution, and the resulting mixture was heated under reflux for 5.5 hours. At the end of this time, the reaction mixture was extracted twice, each time with 100 ml of ethyl acetate. The combined extracts were washed with water, and the solvent was then removed from the extract by distillation under reduced pressure to afford 10.5 g of the title compound as an oil. Nuclear Magnetic Resonance Spectrum (CDCl3, 60 MHz), δ ppm: 1.43 (3H, singlet); 1.63-2.27 (2H, multiplet); 2.03 (3H, singlet); 2.13 (3H, singlet); 2.20 (3H, singlet); 2.43-2.90 (2H, multiplet); 4.00 (2H, singlet); 4.63 (2H, singlet); 6.97 (2H, doublet, J=9 Hz); 7.10-7.60 (5H, multiplet); 7.77 (2H, doublet, J=9 Hz); 9.77 (1H, singlet).

Workup

  1. temperaturewas cooled in an atmosphere of nitrogen
  2. additionto the cooled solution were then added dropwise
  3. temperaturewhilst ice-cooling
  4. temperaturethe resulting mixture was heated
  5. temperatureunder reflux for 5.5 hours
  6. extractionAt the end of this time, the reaction mixture was extracted twice
  7. washThe combined extracts were washed with water
  8. customthe solvent was then removed from the
  9. extractionextract by distillation under reduced pressure

Sources & evidence

ORD record
ord-44b7f6d1934e489fa8732ce2e741c689
Source dataset
uspto-grants-1995_02
Patent number
US05387596

Reaction notes

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