Thionyl Chloride → 1-(Benzyloxy)-4-(chloromethyl)-2-methoxybenzene

HRID 1860672Notes

Reaction equation

HRID 1860672 reaction equation
S(Cl)([Cl:3])=O.[CH2:5]([O:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17]O)=[CH:15][C:14]=1[O:21][CH3:22])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>CCOCC>[CH2:5]([O:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][Cl:3])=[CH:15][C:14]=1[O:21][CH3:22])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 988324-Benzyloxy-3-methoxybenzyl alcohol

Product 1

HCID 2979621-(Benzyloxy)-4-(chloromethyl)-2-methoxybenzeneYield 75.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Thionyl chloride (5.95 g, 50.0 mmol) was added to a mixture of 4-benzyloxy-3-methoxybenzylalcohol (10.0 g, 40.9 mmol) in 50 ml ether at room temperature. The reaction turned into a clear solution and was monitored by TLC. The reaction was quenched with H2O. The product was extracted with ether. The aqueous layer was extracted with ether. The combined organic layer washed with 5% NaHCO3, brine and dried with Na2SO4. Ether was evaporated and the residue was purified by chromatography (on silica gel, ethyl acetate/hexane=2/8) to give a white solid 8.10 g. NMR spectra of the product were consistent for the proposed structure.

Workup

  1. customThe reaction was quenched with H2O
  2. extractionThe product was extracted with ether
  3. extractionThe aqueous layer was extracted with ether
  4. washThe combined organic layer washed with 5% NaHCO3, brine
  5. dry with materialdried with Na2SO4
  6. customEther was evaporated
  7. customthe residue was purified by chromatography (on silica gel, ethyl acetate/hexane=2/8)

Sources & evidence

ORD record
ord-9b95b684a3964a60965a8fe25b71b164
Source dataset
uspto-grants-2003_03
Patent number
US06531494B1

Reaction notes

Loading…