4-Aminobenzophenone → HCID 21469839, compound

HRID 1938649Notes

Reaction equation

HRID 1938649 reaction equation
[NH2:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[CH2:16]([Mg]Cl)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[Cl-].[NH4+]>C(OCC)C>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)([OH:7])[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 143464-AminobenzophenoneHCID 25517Ammonium ChlorideHCID 178418336HCID 178418336, compound

Product 1

HCID 21469839HCID 21469839, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Combine 4-aminobenzophenone (50 g, 0.25 mol) and diethyl ether (500 mL). Slowly, add benzylmagnesium chloride (1 L of a 1M solution in diethyl ether over 1.5 hours. After 18 hours, pour the reaction onto ice and an aqueous solution of ammonium chloride. Separate the layers, extract the organic layer with water, dry over MgSO4, filter, and evaporate in vacuo to give a residue. Recrystallize from isopropanol to give 1-(4-aminophenyl)-1,2-diphenyl-ethanol: mp; 105°-107° C.

Workup

  1. additionpour
  2. customthe reaction onto ice
  3. customSeparate the layers
  4. extractionextract the organic layer with water
  5. dry with materialdry over MgSO4
  6. filtrationfilter
  7. customevaporate in vacuo
  8. customto give a residue
  9. customRecrystallize from isopropanol

Sources & evidence

ORD record
ord-32da0caae495482f9f1011e3ce01b599
Source dataset
uspto-grants-1997_12
Patent number
US05693674

Reaction notes

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