Benzyl Bromide → 5-Benzyloxy-3-chloroxanthone

HRID 2286906Notes

Reaction equation

HRID 2286906 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:17])[C:7]3[C:12]([O:13][C:14]=2[CH:15]=1)=[C:11]([OH:16])[CH:10]=[CH:9][CH:8]=3.[H-].[Na+].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CN(C)C=O>[CH2:20]([O:16][C:11]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:12]=1[O:13][C:14]1[CH:15]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=1[C:6]2=[O:17])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 23460502HCID 23460502, compound

Product 1

HCID 234605165-Benzyloxy-3-chloroxanthone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

The 3-chloro-5-hydroxyxanthone (11 g.) in dimethylformamide (50 ml.) is added to a suspension of sodium hydride (1.5 g.) in dimethylformamide (100 ml.). The mixture is stirred at room temperature for 15 minutes and benzyl bromide (6 ml.) is added dropwise. The mixture is poured into water/ice (600 ml.), extracted with chloroform and the chloroform extract dried with MgSO4. Evaporation of the solvent gives a lightbrown solid which is recrystallised from ethanol to give 5-benzyloxy-3-chloroxanthone, m.p. 154° C.

Workup

  1. extractionextracted with chloroform
  2. extractionthe chloroform extract
  3. dry with materialdried with MgSO4
  4. customEvaporation of the solvent
  5. customgives a lightbrown solid which
  6. customis recrystallised from ethanol

Sources & evidence

ORD record
ord-aef741bfa33b4dee97996a90542351f8
Source dataset
uspto-grants-1981_05
Patent number
US04268514

Reaction notes

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