Ethanol → HCID 12753177, compound

HRID 1733289Notes

Reaction equation

HRID 1733289 reaction equation
[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].O[CH2:14][C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:16].[CH2:23](O)C>O>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH:9]2[C:14](=[CH2:23])[C:15](=[O:16])[C:17]3[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=3)[O:10]2)=[CH:11][CH:12]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 702EthanolHCID 68490alpha-HydroxyacetophenoneHCID 703244-tert-Butylbenzaldehyde

Product 1

HCID 12753177HCID 12753177, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 22.7 g (0.14 mol) of 4-t-butylbenzaldehyde, 19 g (0.14 mol) of 2-hydroxyacetophenone, 38 g (0.1 mol) of borax, 250 ml of H2O and 150 ml of ethanol was refluxed for one day. The reaction was cooled and diluted with an equal volume of H2O and extracted with ether. The ether was washed with brine, dried over anhydrous Na2SO4, filtered, and evaporated to give a brown oil. The oil was chromatographed on 1200 g of silica gel, eluting with benzene. The desired product was obtained as an oil. Recrystallization from petroleum ether gave 2.8 g of 4'-t-butyl flavanone as white crystals, m.p. 103°-104° C.

Workup

  1. temperaturewas refluxed for one day
  2. temperatureThe reaction was cooled
  3. extractionextracted with ether
  4. washThe ether was washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customto give a brown oil
  9. customThe oil was chromatographed on 1200 g of silica gel
  10. washeluting with benzene

Sources & evidence

ORD record
ord-76842c2c773b4cf38aba537cdd5906c3
Source dataset
uspto-grants-1980_12
Patent number
US04241069

Reaction notes

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