Hydrochloric Acid → 7-Phenylhept-5-ynoic acid

HRID 1995773Notes

Reaction equation

HRID 1995773 reaction equation
[C:1]([OH:8])(=[O:7])[CH2:2][CH2:3][CH2:4][C:5]#[CH:6].C([Mg]Br)C.C([Cu])#N.[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.Cl>O1CCCC1>[C:17]1([CH2:16][C:6]#[C:5][CH2:4][CH2:3][CH2:2][C:1]([OH:8])=[O:7])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 1430365-Hexynoic acidHCID 178418443HCID 178418443, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 204880087-Phenylhept-5-ynoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
5 °C

Procedure

Hex-5-ynoic acid (0.1 mole) is added to a tetrahydrofuran solution of ethylmagnesium bromide (0.2 mole) maintained at 5° C. When the addition is complete, the solution is warmed to room temperature and CuCN (0.5 g) is added with stirring. After 20 minutes, a solution of benzylbromide (0.05 mole) in tetrahydrofuran is added dropwise over a one-half hour period. The reaction is maintained at room temperature until thin layer chromatography shows completion and then poured onto 1 N hydrochloric acid. This mixture is then extracted with ethyl ether and the ether layer separated. Removal of the ether gives a residue which is distilled under reduced pressure to afford the title product, 7-phenylhept-5-ynoic acid.

Workup

  1. additionWhen the addition
  2. temperaturethe solution is warmed to room temperature
  3. temperatureThe reaction is maintained at room temperature until thin layer chromatography
  4. extractionThis mixture is then extracted with ethyl ether
  5. customthe ether layer separated
  6. customRemoval of the ether
  7. customgives a residue which
  8. distillationis distilled under reduced pressure

Sources & evidence

ORD record
ord-d94972bf38b84c59aeb949669e12f48d
Source dataset
uspto-grants-1983_09
Patent number
US04405810

Reaction notes

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