p-Toluenesulfonic acid → HCID 86743282, compound

HRID 1722234Notes

Reaction equation

HRID 1722234 reaction equation
[Br:1]/[C:2](=[CH:10]/[CH2:11][CH2:12][C:13]#[C:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)/[C:3]([O:5]C(C)(C)C)=[O:4].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1.CCOCC>[Br:1]/[C:2](=[CH:10]/[CH2:11][CH2:12][C:13]#[C:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)/[C:3]([OH:5])=[O:4]

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 86743283HCID 86743283, compound

Product 1

HCID 86743282HCID 86743282, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of t-butyl 2-bromo-7-phenyl-(2E)-hepten-6-ynoate (1.5 g, 4.48 mmol) and 4-toluenesulphonic acid (0.1 g) in dry benzene (15 ml) was heated under reflux under dry nitrogen for 2 hours. The cooled mixture was diluted with ether and the organic phase was extracted with aqueous sodium bicarbonate. The aqueous phase was acidified and extracted with ether. The organic phase was washed with brine and dried over magnesium sulphate. The solvents were removed to give 0.95 g (76% of theory) of 2-bromo-7-phenyl-(2E)-hepten-6-ynoic acid as a colourless solid.

Workup

  1. temperatureunder reflux under dry nitrogen for 2 hours
  2. extractionthe organic phase was extracted with aqueous sodium bicarbonate
  3. extractionextracted with ether
  4. washThe organic phase was washed with brine
  5. dry with materialdried over magnesium sulphate
  6. customThe solvents were removed

Sources & evidence

ORD record
ord-6225af415b5e4ccbbf0ab12a0267e19a
Source dataset
uspto-grants-1989_08
Patent number
US04855086

Reaction notes

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