Benzyl Chloride → HCID 20211972, compound

HRID 1906668Notes

Reaction equation

HRID 1906668 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][C:3]=1[CH3:11].[CH2:12](Cl)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C.ClCCl>[CH2:12]([O:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][C:3]=1[CH3:11])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 10130055HCID 10130055, compound

Product 1

HCID 20211972HCID 20211972, compoundYield 90.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

2-(4-Hydroxy-3-methylphenyl)ethanol (18 g), benzyl chloride (15.4 g) and anhydrous potassium carbonate (90 g) were stirred under reflux in methyl ethyl ketone (500 ml) for 20 hours. The reaction mixture was cooled and evaporated under reduced pressure to give an oily residue. This residue was dissolved in dichloromethane, washed with 2N sodium hydroxide (2×), washed with brine (2×), dried (MgSO4), and evaporated under reduced pressure to give an oil. This was triturated under petroleum ether (40°-60°) (200 ml) with cooling to afford 2-(4-benzyloxy-3-methylphenyl)ethanol as a white solid (26.0 g).

Workup

  1. temperatureThe reaction mixture was cooled
  2. customevaporated under reduced pressure
  3. customto give an oily residue
  4. washwashed with 2N sodium hydroxide (2×)
  5. washwashed with brine (2×)
  6. dry with materialdried (MgSO4)
  7. customevaporated under reduced pressure
  8. customto give an oil
  9. customThis was triturated under petroleum ether (40°-60°) (200 ml)
  10. temperaturewith cooling

Sources & evidence

ORD record
ord-bbdf5f490ba84220a5081eded731c85b
Source dataset
uspto-grants-1987_03
Patent number
US04652563

Reaction notes

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