Diethylene Glycol → HCID 12218409, compound

HRID 1873216Notes

Reaction equation

HRID 1873216 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH:16]=O.O.NN.C(O)COCCO.[OH-].[K+]>O>[CH2:10]([C:2]1[O:1][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=1)[C:15]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:16]=1

Participants

6

Reactant 4

HCID 8117Diethylene GlycolHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 18357511HCID 18357511, compound

Product 1

HCID 12218409HCID 12218409, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of 2-benzofuranylphenyl-methanone (34.8 g, 0.157 mol), hydrazine monohydrate (31 mL, 0.639 mol) and diethylene glycol (72 mL) was heated to reflux for 10 min and cooled to room temperature. Potassium hydroxide (22.9 g, 0.408 mol) was added. The reaction mixture was heated in 130° C. oil bath for 1 h., cooled to room temperature and added to water. The oil was extracted with ether. Silica ge was added to the ether phase and the solvent was removed. The adsorbate was flash chromatographed eluent: (petroleum ether) to provide the title compound as an oil (23.9 g, 90%): NMR (CDCl3); δ7.5-7.1 (m, 9 H), 6.38 (s, 1 H), 4.10 (s, 2 H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 10 min
  3. temperatureThe reaction mixture was heated in 130° C. oil bath for 1 h.
  4. temperaturecooled to room temperature
  5. extractionThe oil was extracted with ether
  6. additionSilica ge was added to the ether phase
  7. customthe solvent was removed
  8. customchromatographed eluent

Sources & evidence

ORD record
ord-60ef49962f1141eeb33b88e6c0c99252
Source dataset
uspto-grants-2000_08
Patent number
US06110962

Reaction notes

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