Hexane → HCID 178444390, compound

HRID 1982115Notes

Reaction equation

HRID 1982115 reaction equation
[Br:1][C:2]([Br:5])(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:25]([C@H:30]1[CH2:35][CH2:34][C@H:33]([CH:36]=O)[CH2:32][CH2:31]1)[CH2:26][CH2:27][CH2:28][CH3:29].CCCCCC>C(Cl)Cl>[Br:1][C:2]([Br:5])=[CH:36][C@H:33]1[CH2:34][CH2:35][C@H:30]([CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:31][CH2:32]1

Participants

6

Reactant 4

HCID 8058HexaneHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 178444538HCID 178444538, compound

Product 1

HCID 178444390HCID 178444390, compoundYield 77.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

A solution, cooled to 0° C., of 90.9 g of tetrabromomethane in 100 ml of methylene chloride was treated under argon gasification within 20 minutes with a solution of 143.9 g of triphenylphosphine in 200 ml of methylene chloride. The clear orange solution was stirred at 0° C. for a further 5 minutes and then treated dropwise within 10 minutes at 0° C. with a solution of 25 g of trans-4-pentylcyclohexanecarboxaldehyde (purity about 82%) in 80 ml of methylene chloride. After stirring at 0° C. for 30 minutes, the mixture was poured into 2.5 l of hexane and the precipitate which separated was filtered off. The filtrate was concentrated, digested with 1 l of hexane, filtered and again concentrated. Low-pressure chromatography (0.5 bar) of the residue (52.7 g) on silica gel with hexane gave 35.9 g (77.4%) of trans-1-(2,2-dibromovinyl)-4-pentylcyclohexane as a colourless oil; Rf-value (hexane) 0.58.

Workup

  1. stirringAfter stirring at 0° C. for 30 minutes
  2. customthe precipitate which separated
  3. filtrationwas filtered off
  4. concentrationThe filtrate was concentrated
  5. filtrationfiltered
  6. concentrationagain concentrated

Sources & evidence

ORD record
ord-c19dd4c1e1774e35bbf892bfff4feef6
Source dataset
uspto-grants-1986_06
Patent number
US04595521

Reaction notes

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