Carbon tetrabromide → 1-Octyl-4-(prop-2-YN-1-YL)benzene

HRID 1995774Notes

Reaction equation

HRID 1995774 reaction equation
[CH2:1]([C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH:16]=O)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[C:18](Br)(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([Li])CCC>C(Cl)Cl.C(OCC)C.O1CCCC1.[Zn]>[CH2:1]([C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]#[CH:18])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

9

Reactant 4

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 53716894(4-Octylphenyl)acetaldehydeHCID 178418339Butyllithium

Product 1

HCID 204880011-Octyl-4-(prop-2-YN-1-YL)benzene

Reagents, catalysts & solvents 4

HCID 23994ZincCatalystHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

p-(n-Octyl)phenylacetaldehyde (1 mmole, prepared as described in paragraph A of this example) is dissolved in methylene chloride, and treated with carbontetrabromide (4 mmole), triphenylphosphine (4 mmole) and zinc dust (4 mmole) at room temperature. The reaction mixture is then diluted with ethyl ether and filtered. The filtrate is washed with water, dried and evaporated to give an oily residue. This residue is dissolved in tetrahydrofuran and treated with n-butyl lithium (2.1 mmole) at -78° C. for one hour and then at room temperature until the reaction ceases. The reaction mixture is poured onto water, the pH adjusted to 7, and extracted with methylene chloride. The methylene chloride extract is washed with water, dried and the solvent removed by evaporation. Distillation under reduced pressure affords p-(n-octyl)benzylacetylene.

Workup

  1. filtrationfiltered
  2. washThe filtrate is washed with water
  3. customdried
  4. customevaporated
  5. customto give an oily residue
  6. customat room temperature until the reaction ceases
  7. additionThe reaction mixture is poured onto water
  8. extractionextracted with methylene chloride
  9. extractionThe methylene chloride extract
  10. washis washed with water
  11. customdried
  12. customthe solvent removed by evaporation
  13. distillationDistillation under reduced pressure

Sources & evidence

ORD record
ord-b1dcac1cb3234f2496aece6f12c3f42f
Source dataset
uspto-grants-1983_09
Patent number
US04405810

Reaction notes

Loading…