Thionyl Chloride → HCID 21221127, compound

HRID 1377188Notes

Reaction equation

HRID 1377188 reaction equation
[CH3:1][C:2]1[C:9]([CH3:10])=[C:8]([O:11][CH3:12])[CH:7]=[CH:6][C:3]=1[CH2:4]O.C1OC2C=CC(C[Cl:19])=CC=2O1.S(Cl)(Cl)=O>CCOCC>[CH3:1][C:2]1[C:9]([CH3:10])=[C:8]([O:11][CH3:12])[CH:7]=[CH:6][C:3]=1[CH2:4][Cl:19]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 887131,3-Benzodioxole, 5-(chloromethyl)-HCID 43971742,3-Dimethyl-4-methoxybenzyl alcohol

Product 1

HCID 21221127HCID 21221127, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1 g (6.016 mmol) of 2,3-dimethyl-4-methoxybenzyl alcohol (Aldrich, Steinheim, FRG) and 4.8 g of diisopropylaminomethylpolystyrene (polyhunig base, see Ex. 44a) in 21 ml of abs. ether are treated dropwise, at from 0° C. to 5° C. and over the space of approximately 25 min, with 0.482 ml of thionyl chloride. After the reaction has ended, the mixture is filtered with suction and the solvent and the excess reagent are removed. The residue, which is the desired title compound, is subjected, without purification, to further processing. TLC Rf (hexane:ethyl acetate 4:1)=0.59. IR(CH2Cl2) inter alia: 1599, 1485, 1466 und 1107 cm-1. 1H-NMR (200 MHz, CDCl3): 7.14 (d, 1H); 6.69 (d, 1H); 4.64 (s, 2H); 3.82, 2.34 and 2.18 (each s, each 3H).

Workup

  1. filtrationthe mixture is filtered with suction
  2. customthe solvent and the excess reagent are removed
  3. customis subjected, without purification, to further processing

Sources & evidence

ORD record
ord-9149e4903598427287ac57559a58efc6
Source dataset
uspto-grants-1997_09
Patent number
US05663200

Reaction notes

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