Formaldehyde → Ethyl acetate hexane

HRID 2219222Notes

Reaction equation

HRID 2219222 reaction equation
C=O.N1[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1.[C:9]1([OH:15])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(O)C>[CH3:13][CH2:14][CH2:9][CH2:10][CH2:11][CH3:12].[CH3:4][CH2:5][O:6][C:7]([CH3:8])=[O:15]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 996PhenolHCID 8083Morpholine

Product 1

HCID 21226206Ethyl acetate hexaneYield 40%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of paraformaldehyde (3.24 g, 108 mmol) and morpholine (9.40 mL, 108 mmol) in ethanol (40 mL) was stirred at room temperature for 30 minutes, and then a solution of the corresponding phenol 6a, 6b (106 mmol) in 20 mL of ethanol was added and the mixture was refluxed overnight. After cooling, the solvent was evaporated, and the crude product 7a, 7b was purified by chromatography in silica gel, eluent hexane/EtOAc 9:1 (40-65% yield).

Workup

  1. temperaturethe mixture was refluxed overnight
  2. temperatureAfter cooling
  3. customthe solvent was evaporated
  4. customthe crude product 7a, 7b was purified by chromatography in silica gel

Sources & evidence

ORD record
ord-b90d3d2287334236a5febd2220c92edc
Source dataset
uspto-grants-2008_08
Patent number
US07414063B2

Reaction notes

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