4-Aminobenzophenone → HCID 21469839, compound

HRID 2295153Notes

Reaction equation

HRID 2295153 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-e082e3f9b020415eb542ba7b59ef4bf7
Source dataset
uspto-grants-1997_11
Patent number
US05691384

Reaction notes

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