Benzoyl chloride → HCID 68966117, compound

HRID 2410620Notes

Reaction equation

HRID 2410620 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][OH:14].[N].[C:16](Cl)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>N1C=CC=CC=1>[C:16]([O:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][Br:1])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 178520590HCID 178520590, compound

Product 1

HCID 68966117HCID 68966117, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In a 100 mL two-neck flask under a static head of nitrogen 12-bromo-dodecanol (5.0 g, 18.9 mmol) is weighed, pyridine (25 mL) is added and the whole is brought to 0° C. with an external bath of ice and salt. Benzoyl chloride is dripped slowly and, when adding is finished, the ice bath is removed and the whole is left stirring at room temperature. After 18 hours ethyl acetate (100 mL) and distilled water (100 mL) are added. The organic phase is washed 3 times with distilled water (3×50 mL) and anhydrified on anhydrous sodium sulphate. It is filtered under a vacuum and the solvent is eliminated in the Rotovapor and in the high vacuum pump. The product is purified with column chromatography on silica gel with an eluant mixture of petroleum ether/ethylic ether 5/1. 4.5 g of 12-bromododecyl benzoate are isolated as a colourless oil with a yield of 65%.

Workup

  1. customthe whole is brought to 0° C. with an external bath of ice and salt
  2. additionwhen adding
  3. customthe ice bath is removed
  4. waitthe whole is left
  5. distillationdistilled water (100 mL)
  6. additionare added
  7. washThe organic phase is washed 3 times with distilled water (3×50 mL)
  8. filtrationIt is filtered under a vacuum
  9. customThe product is purified with column chromatography on silica gel with an eluant mixture of petroleum ether/ethylic ether 5/1

Sources & evidence

ORD record
ord-297b26d7ea33448f8e313ef58d8e4a61
Source dataset
uspto-grants-2014_08
Patent number
US08816107B2

Reaction notes

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