4-Chlorobenzaldehyde → HCID 11435538, compound

HRID 2290176Notes

Reaction equation

HRID 2290176 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[Mg].Br[CH2:12][CH2:13][CH:14]=[CH2:15].[Cl-].[NH4+]>CCOCC>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]([OH:7])[CH2:15][CH2:14][CH:13]=[CH2:12])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 77264-ChlorobenzaldehydeHCID 21241Homoallyl bromideHCID 25517Ammonium ChlorideHCID 5462224Magnesium

Product 1

HCID 11435538HCID 11435538, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 70 g (0.5 mole) of 4-chlorobenzaldehyde in 100 ml of absolute ether is added dropwise to a Grignard solution of 12.2 g (0.5 mole) of magnesium and 67.5 g (0.5 mole) of 4-bromo-1-butene in 350 ml of absolute ether, with stirring, and, when the addition has ended, the mixture is heated at the reflux temperature for 2 hours. The cooled reaction mixture is poured into a mixture of 1 liter of saturated ammonium chloride solution and ice, the organic phase is separated off, washed twice with water, dried over sodium sulphate and concentrated in vacuo and the residue is then distilled under a high vacuum. 50 g (58% of theory) of 5-(4-chlorophenyl)-pent-1-en-5-ol of boiling point 100° C.-105° C./0.13 mbar are obtained.

Workup

  1. additionwhen the addition
  2. temperaturethe mixture is heated at the reflux temperature for 2 hours
  3. customThe cooled reaction mixture
  4. customthe organic phase is separated off
  5. washwashed twice with water
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated in vacuo
  8. distillationthe residue is then distilled under a high vacuum

Sources & evidence

ORD record
ord-f64756b91c5f41389ca833376dd80203
Source dataset
uspto-grants-1986_10
Patent number
US04615725

Reaction notes

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