Diethyl Ether → HCID 19037658, compound

HRID 263486Notes

Reaction equation

HRID 263486 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC[O:11][CH2:12][CH3:13]>C1C=CC=CC=1>[C:1]1([CH:3]2[CH2:2][CH:1]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:6][CH2:13][C:12]2=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 3283Diethyl EtherHCID 178418255HCID 178418255, compound

Product 1

HCID 19037658HCID 19037658, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The oil was dissolved in 400 mL benzene and added dropwise over 40 minutes to 83 mL (250 mmol) of a 3.0M solution of phenylmagnesium bromide in ether, cooling so the temperature did not rise above 10° C. The reaction was then allowed to warm and heated to reflux for 14 hours. It was then cooled, quenched with aqueous ammonium chloride solution, then washed with water and brine, dried over sodium sulfate, and evaporated. The yield was 53.9 g (approximately theoretical), and the crude oil was used directly in the next step.

Workup

  1. temperaturecooling so the temperature
  2. customdid not rise above 10° C
  3. temperatureto warm
  4. temperatureheated
  5. temperatureto reflux for 14 hours
  6. temperatureIt was then cooled
  7. customquenched with aqueous ammonium chloride solution
  8. washwashed with water and brine
  9. dry with materialdried over sodium sulfate
  10. customevaporated

Sources & evidence

ORD record
ord-64871aed8d704c32a7a5185e9edc41dc
Source dataset
uspto-grants-1997_07
Patent number
US05643904

Reaction notes

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