Benzyl Bromide → HCID 6461349, compound

HRID 1066496Notes

Reaction equation

HRID 1066496 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH2:7])=[O:6].[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+].C(Cl)Cl.CO>CC(C)=O.CCCCCC>[CH2:11]([O:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH2:7])=[O:6])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 3424033-HydroxybenzamideHCID 21226129Dichloromethane methanol

Product 1

HCID 6461349HCID 6461349, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8058HexaneSolvent

Procedure

To a solution of 13.7 g of 3-hydroxybenzamide and 25.6 of benzyl bromide in acetone (400 ml) were added 25.6 g of potassium carbonate at RT. The mixture was then refluxed for 6 h after which time the reaction was completed according to TLC analysis (CH2Cl2/MeOH: 20/1). The reaction mixture was cooled to RT and partitioned between EtOAc and water, the organic layer was separated, dried over sodium sulphate and concentrated in vacuo. The crystalline residue obtained was suspended in n-hexane (200 ml), the crystals were filtered off under suction and dried in a vacuum to give 3-benzyloxy-benzamide as a white crystalline solid, mp 136°-140° C.

Workup

  1. temperatureThe mixture was then refluxed for 6 h after which time the reaction
  2. custompartitioned between EtOAc and water
  3. customthe organic layer was separated
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated in vacuo
  6. customThe crystalline residue obtained
  7. filtrationthe crystals were filtered off under suction
  8. customdried in a vacuum

Sources & evidence

ORD record
ord-09aca3f6a7064aa6bc245c5d9ae0d166
Source dataset
uspto-grants-2001_06
Patent number
US06242601B1

Reaction notes

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