Formaldehyde → HCID 56991944, compound

HRID 864656Notes

Reaction equation

HRID 864656 reaction equation
[CH3:1][C:2]([C:5]1[CH:6]=[C:7]([CH2:16][CH:17]([SH:21])[C:18](O)=[O:19])[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])[CH3:3].C=O.[CH2:24]([NH2:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[C:32](OCC)(=O)C>C1(C)C=CC=CC=1>[CH3:13][C:12]([C:9]1[CH:8]=[C:7]([CH2:16][CH:17]2[S:21][CH2:32][N:31]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:18]2=[O:19])[CH:6]=[C:5]([C:2]([CH3:3])([CH3:1])[CH3:4])[C:10]=1[OH:11])([CH3:14])[CH3:15]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 7504BenzylamineHCID 8857Ethyl Acetate2×HCID 11023322HCID 11023322, compound

Product 1

HCID 56991944HCID 56991944, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3-[3,5-bis-(1,1-dimethylethyl)-4-hydroxyphenyl]-2-mercaptopropanoic acid (4.58 g; 14.75 mmole), prepared substantially in accordance with the method described in Example 1A, was suspended in 50 ml of toluene. Under a nitrogen atmosphere, 0.45 g (15.0 mmoles) of paraformaldehyde was added followed by 1.67 grams (15.56 mmoles) of benzylamine. The resulting solution was heated at reflux temperature for one hour with removal of water by means of a Dean-Stark apparatus. The solution was allowed to cool to room temperature. Fifty milliliters of ethyl acetate was added and the resultant clear, yellow solution was extracted with 35 ml of a 0.5N hydrochloric acid solution, resulting in a cloudy yellow organic layer. An additional 30 ml of ethyl acetate was added to the cloudy organic layer and the resulting solution was extracted again with 35 ml of a 0.5N hydrochloric acid solution, resulting in yet another cloudy organic layer. Fifteen milliliters of ethyl acetate was added to the cloudy organic layer which was then washed with 30 ml of a 1:1 bicarbonate/brine solution, followed by 30 ml of a brine solution. The resulting solution was then dried with sodium sulfate, filtered and evaporated to provide 7.2 g of a viscous, cloudy oil.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureat reflux temperature for one hour
  3. customwith removal of water by means of a Dean-Stark apparatus
  4. additionFifty milliliters of ethyl acetate was added
  5. extractionthe resultant clear, yellow solution was extracted with 35 ml of a 0.5N hydrochloric acid solution
  6. customresulting in a cloudy yellow organic layer
  7. extractionthe resulting solution was extracted again with 35 ml of a 0.5N hydrochloric acid solution
  8. customresulting in yet another cloudy organic layer
  9. washwas then washed with 30 ml of a 1:1 bicarbonate/brine solution
  10. dry with materialThe resulting solution was then dried with sodium sulfate
  11. filtrationfiltered
  12. customevaporated
  13. customto provide 7.2 g of a viscous, cloudy oil

Sources & evidence

ORD record
ord-686672c296384961a1c38f63ad6c4a61
Source dataset
uspto-grants-1996_10
Patent number
US05563277

Reaction notes

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