Tetrahydrofuran → 6-Bromohexyl cinnamate

HRID 29739

Reaction equation

HRID 29739 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][OH:8].C1COCC1.[C:14](Cl)(=[O:23])[CH:15]=[CH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(N(CC)CC)C>[C:14]([O:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][Br:1])(=[O:23])[CH:15]=[CH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 660233-Phenylprop-2-enoyl chlorideHCID 779706-Bromo-1-hexanol

Product 1

HCID 688496286-Bromohexyl cinnamateYield 53%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

7 g of 6-bromohexanol was dissolved in a mixed solution of 5 ml of triethylamine as base and 50 ml of THF, and then, cinnamoyl chloride was added dropwise thereto at 0° C. The resultant was filtered to remove the solvent and the residue was purified with a SiO2 column chromatography (EA:n-Hexane=1:5) to obtain 8 g of 6-bromohexyl cinnamate (yield: 53%).

Workup

  1. customat 0° C
  2. filtrationThe resultant was filtered
  3. customto remove the solvent
  4. customthe residue was purified with a SiO2 column chromatography (EA:n-Hexane=1:5)

Sources & evidence

ORD record
ord-6c427d124c894c5b946a8d05df74ed6e
Source dataset
uspto-grants-2008_09
Patent number
US07422778B2

Linked notes

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