Thionyl Chloride → 2-(Chloromethyl)anisole

HRID 2394145Notes

Reaction equation

HRID 2394145 reaction equation
S(Cl)(Cl)=O.[CH3:5][O:6][C:7]1[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=1[CH2:9]O.C1OC2C=CC(C[Cl:21])=CC=2O1>CCOCC>[CH3:5][O:6][C:7]1[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=1[CH2:9][Cl:21]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 691542-Methoxybenzyl alcoholHCID 887131,3-Benzodioxole, 5-(chloromethyl)-

Product 1

HCID 814952-(Chloromethyl)anisole

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

16.8 ml of thionyl chloride are added dropwise, over the space of approximately 30 min, to 10 ml of 2-methoxybenzyl alcohol (Fluka, Buchs, Switzerland) and 53.76 g of diisopropylaminomethylpolystyrene (polyhunig base, see Ex. 44a)) in 200 ml of abs. ether. After the mixture has been stirred at 0° C. for a further 1.5 h, it is filtered with suction and the filtrate is concentrated on a RE and under HV. The residue is purified by chromatography on silica gel (eluent: hexane/ethyl acetate, 6:1). TLC Rf (hexane:ethyl acetate=4:1)=0.5. 1H-NMR (200 MHz, CDCl3): 7.42-7.24 (m, 2H); 7.0-6.84 (m, 2H); 4.68 (s, 2H); 3.9 (s, 3H).

Workup

  1. filtrationit is filtered with suction
  2. concentrationthe filtrate is concentrated on a RE and under HV
  3. customThe residue is purified by chromatography on silica gel (eluent: hexane/ethyl acetate, 6:1)

Sources & evidence

ORD record
ord-277ccc709a114c0a9a9e8590693063f5
Source dataset
uspto-grants-1998_09
Patent number
US05807891

Reaction notes

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