Bromoform → HCID 21433718, compound

HRID 2398708Notes

Reaction equation

HRID 2398708 reaction equation
[CH:1]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.[CH:15](Br)([Br:17])[Br:16].[OH-].[Na+]>[Cl-].C([N+](C(CCCCCC)C)(C(CCCCCC)C)C)(CCCCCC)C.ClCCl>[Br:16][C:15]1([Br:17])[CH:14]2[CH:1]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]2

Participants

6

Reactant 3

HCID 5558BromoformHCID 14798Sodium HydroxideHCID 138767HCID 138767, compound

Product 1

HCID 21433718HCID 21433718, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 12783666HCID 12783666, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

Cyclotetradecene (40 g), bromoform (75.9 g), 50% aqueous sodium hydroxide solution (300 ml), dichloromethane (20 ml), tri-sec-octyl methylammonium chloride (1 drop) and 1 drop of a long-chain alcohol ethoxylate of the structure [C14-15 ] [OC2 ]11 --OH (Dobanol 45 + 11 EO, Shell Chemicals) were stirred together at 40° C. for 7 hours. The organic layer was separated and the volatile organic components removed under reduced pressure. The residue was dissolved in pentane and the solution was stirred with active charcoal (Norit). The solution was filtered and the pentane removed under reduced pressure to give the required product in almost 100% yield.

Workup

  1. customThe organic layer was separated
  2. customthe volatile organic components removed under reduced pressure
  3. dissolutionThe residue was dissolved in pentane
  4. filtrationThe solution was filtered
  5. customthe pentane removed under reduced pressure

Sources & evidence

ORD record
ord-5f78a3942ce74af690f2dbea25b3926d
Source dataset
uspto-grants-1977_05
Patent number
US04025562

Reaction notes

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