Formaldehyde → HCID 15117885, compound

HRID 2107749Notes

Reaction equation

HRID 2107749 reaction equation
[OH:1][CH2:2][CH:3]1[O:7][C:6]([CH2:9][O:10][C:11]2[CH:16]=[C:15]([C:17]([CH2:20][C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:19])[CH3:18])[CH:14]=[CH:13][C:12]=2[OH:25])([CH3:8])[CH2:5][CH2:4]1.[NH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1.[CH2:32]=O>C(O)(C)C>[OH:1][CH2:2][CH:3]1[O:7][C:6]([CH2:9][O:10][C:11]2[CH:16]=[C:15]([C:17]([CH2:20][C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:18])[CH3:19])[CH:14]=[C:13]([CH2:32][N:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)[C:12]=2[OH:25])([CH3:8])[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 8083MorpholineHCID 15117876HCID 15117876, compound

Product 1

HCID 15117885HCID 15117885, compoundYield 51.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 3.7 g (10 mmole) of 2-(5-hydroxymethyl-2-methyl-2-tetrahydrofuranylmethoxy)-4-t-octylphenol, 1 ml (12 mmole) of morpholine and 0.35 g (12 mmole) of paraformaldehyde in 25 ml of isopropanol was heated under reflux for 18 hours. The solvent was removed by evaporation in vacuo and the residue was extracted with diethyl ether. The resulting ethereal solution was washed with water, followed by saturated sodium chloride solution, and then dried (MgSO4) and evaporated in vacuo. The residue was purified by chromatography over silica gel, eluting with ethyl acetate, to give 2.31 g of the title compound as an oil.

Workup

  1. temperatureunder reflux for 18 hours
  2. customThe solvent was removed by evaporation in vacuo
  3. extractionthe residue was extracted with diethyl ether
  4. washThe resulting ethereal solution was washed with water
  5. dry with materialdried (MgSO4)
  6. customevaporated in vacuo
  7. customThe residue was purified by chromatography over silica gel
  8. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-7b085623097d4306b609242d7a343c86
Source dataset
uspto-grants-1990_06
Patent number
US04935442

Reaction notes

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