Benzyl Alcohol → Benzyl 8-bromooctanoate

HRID 48900

Reaction equation

HRID 48900 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([OH:11])=[O:10].[CH2:12](O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)(Cl)(Cl)Cl.N1(C2C=CN=CC=2)CCCC1>[CH2:12]([O:10][C:9](=[O:11])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][Br:1])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 244Benzyl AlcoholHCID 10868DicyclohexylcarbodiimideHCID 5482758-Bromooctanoic acid

Product 1

HCID 11278409Benzyl 8-bromooctanoate

Reagents, catalysts & solvents 2

HCID 755674-PyrrolidinopyridineCatalystHCID 5943Carbon TetrachlorideSolvent2×

Procedure

There were dissolved 11.6 g (52 mmol) of 8-bromooctanoic acid in 100 ml of CCl4 and around 5° C. (ice bath), there were added to the solution 5.41 g (50 mmol) of benzyl alcohol and 2.5 mmol of 4-pyrrolidino-pyridine catalyst. Thereafter, a solution of 10.73 g (52 mmol) of dicyclohexylcarbodiimide (DCC) in 10 ml of carbon tetrachloride was added portion-wise under stirring. The precipitation of the expected dicyclohexylurea (DCU) was effective after a few min and the temperature was allowed to come back to room temperature. After ½ hr, the reaction was complete as checked by TLC (hexane/ether 1:1). Then after about 1 hr, 0.5 ml of AcOH were added to quench remaining DCC and the DCU was filtered out after about one hour (yield 11.2 g=100%).

Workup

  1. customThe precipitation of the expected dicyclohexylurea (DCU)
  2. customto come back to room temperature
  3. waitThen after about 1 hr
  4. addition0.5 ml of AcOH were added
  5. customto quench
  6. filtrationthe DCU was filtered out after about one hour (yield 11.2 g=100%)

Sources & evidence

ORD record
ord-3f77a10e74bf44d4b323cf8ea0e05ff6
Source dataset
uspto-grants-2004_03
Patent number
US06706280B2

Linked notes

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