Benzyl Chloride → 3,4-Dichlorophenyl benzyl carbinol

HRID 1607209Notes

Reaction equation

HRID 1607209 reaction equation
[Mg].[CH2:2](Cl)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Cl:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][C:18]=1[Cl:19])[CH:14]=[O:15]>C(OCC)C.II>[Cl:10][C:11]1[CH:12]=[C:13]([CH:14]([CH2:2][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[OH:15])[CH:16]=[CH:17][C:18]=1[Cl:19]

Participants

6

Reactant 3

HCID 7503Benzyl ChlorideHCID 227103,4-DichlorobenzaldehydeHCID 5462224Magnesium2×

Product 1

HCID 198527923,4-Dichlorophenyl benzyl carbinolYield 96.8%

Reagents, catalysts & solvents 2

HCID 807IodineCatalystHCID 3283Diethyl EtherSolvent3×

Procedure

Into a 1000 ml three necked flask equiped with a reflux condenser and an addition funnel was placed 8.8 g of magnesium turnings (0.36 mole) and 400 ml of diethyl ether. After activation of the magnesium with 0.02 g of iodine, the mixture was heated to reflux and a solution of 44 g (0.35 mole) of benzyl chloride in ethyl ether was added at a rate to maintain the reflux. When the reaction had subsided, a solution of 50 g (0.29 mole) of 3,4-dichlorobenzaldehyde in 75 ml of diethyl ether was added at a rate to maintain reflux. After 15 minutes, the reaction was quenched with water and acidified with dilute hydrochloric acid. The organic layere was washed with brine, dried, and concentrated in vacuo yielding 75 g of 3,4-dichlorophenyl benzyl carbinol which was used without further purification. NMR data was consistent with the structure.

Workup

  1. temperatureto reflux
  2. temperatureto maintain the reflux
  3. temperatureto maintain
  4. temperaturereflux
  5. customthe reaction was quenched with water
  6. washThe organic layere was washed with brine
  7. customdried
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4cd2748033004d83a1d78c16c6fe102f
Source dataset
uspto-grants-1989_09
Patent number
US04863947

Reaction notes

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