Formaldehyde → HCID 19838448, compound

HRID 1607134Notes

Reaction equation

HRID 1607134 reaction equation
[CH2:1]=O.[CH2:3]([NH:10][CH:11]1[CH2:23][C:22]2[C:14](=[CH:15][C:16]3[CH2:20][CH2:19][O:18][C:17]=3[CH:21]=2)[CH2:13][CH2:12]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>O.C(O)=O.[OH-].[Na+]>[CH2:3]([N:10]([CH:11]1[CH2:23][C:22]2[C:14](=[CH:15][C:16]3[CH2:20][CH2:19][O:18][C:17]=3[CH:21]=2)[CH2:13][CH2:12]1)[CH3:1])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 2

HCID 712FormaldehydeHCID 19838485HCID 19838485, compound

Product 1

HCID 19838448HCID 19838448, compound

Reagents, catalysts & solvents 3

HCID 284Formic AcidSolventHCID 962WaterSolvent2×HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
0 °C

Procedure

44 ml of 37% strength formaldehyde solution in water are added to a solution of 21 g of the compound of Example 7 in 26 ml of concentrated formic acid maintained at 0° C. After 2 hours under reflux, the cooled reaction medium is diluted with 40% strength sodium hydroxide solution in water and extracted with methylene chloride. The organic phase is washed, dried and then evaporated under vacuum. The residue, purified by passage through a silica column, leads to the production of an oil. The elution solvent used is a mixture of methylene chloride and ethyl acetate (85:15 V/V)

Workup

  1. temperatureAfter 2 hours under reflux
  2. customthe cooled reaction medium
  3. extractionextracted with methylene chloride
  4. washThe organic phase is washed
  5. customdried
  6. customevaporated under vacuum
  7. customThe residue, purified by passage through a silica column
  8. additiona mixture of methylene chloride and ethyl acetate (85:15 V/V)

Sources & evidence

ORD record
ord-68666602eaad42cda64f781e2a77d1a9
Source dataset
uspto-grants-1989_09
Patent number
US04863951

Reaction notes

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