Benzyl Bromide → Benzyl 6-bromohexanoate

HRID 1583416Notes

Reaction equation

HRID 1583416 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8].[CH2:10](Br)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 202106-Bromohexanoic acid

Product 1

HCID 562258Benzyl 6-bromohexanoateYield 86.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 50.0 g of 6-bromohexanoic acid, 88 g of benzyl bromide, and 69 g of potassium carbonate in 500 ml of dimethylformamide was stirred overnight at room temperature. The reaction mixture was filtered, concentrated, and the residue was taken up in ether, washed with water and dried over sodium sulfate. The residue obtained after evaporation was distilled to give 63 g (85%) of benzyl 6-bromohexanoate.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. customThe residue obtained
  6. customafter evaporation
  7. distillationwas distilled

Sources & evidence

ORD record
ord-7c5e7dc593a94635bad589ac6d27a767
Source dataset
uspto-grants-1985_11
Patent number
US04551460

Reaction notes

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