Benzyl Alcohol → Benzyl 6-bromohexanoate

HRID 2354039Notes

Reaction equation

HRID 2354039 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8].[CH2:10](O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.ClCCl>[CH2:10]([O:8][C:7](=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][Br:1])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 244Benzyl AlcoholHCID 10868DicyclohexylcarbodiimideHCID 202106-Bromohexanoic acid

Product 1

HCID 562258Benzyl 6-bromohexanoate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 6-bromo-hexanoic acid (0.10 mol), benzyl alcohol (0.10 mol), 4-dimethylaminopyridine (1.78·10−2 mol) and dichloromethane (600 ml) is stirred and kept at 0° C. with an ice bath, then added with N,N′-dicyclohexylcarbodiimide (0.13 mol) and left to react for 16 hours. At the end of the reaction, the solution is filtered and the precipitate is discarded, whilst the solution is repeatedly washed with H2O, discarding the precipitate possibly formed. The organic layers are pooled and washed again with a saturated solution of NaHCO3, a solution of HCl 0.1 M and then with water. The solution is dried with MgSO4, filtered, and the solvent is removed by vacuum evaporation.

Workup

  1. customkept at 0° C. with an ice bath
  2. waitleft
  3. customto react for 16 hours
  4. customAt the end of the reaction
  5. filtrationthe solution is filtered
  6. washis repeatedly washed with H2O
  7. custompossibly formed
  8. washwashed again with a saturated solution of NaHCO3
  9. dry with materialThe solution is dried with MgSO4
  10. filtrationfiltered
  11. customthe solvent is removed by vacuum evaporation

Sources & evidence

ORD record
ord-975ff2f5a3b74265a2f037b9274f3905
Source dataset
uspto-grants-2010_07
Patent number
US07750157B2

Reaction notes

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