Thionyl Chloride → HCID 12979316, compound

HRID 1357035Notes

Reaction equation

HRID 1357035 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[C:12]([O:13][CH3:14])=[CH:11][CH:10]=[CH:9][C:6]=1[CH2:7]O.C(N(CC)C(C)C)(C)C.S(Cl)([Cl:26])=O>C(OCC)C>[CH3:1][O:2][CH2:3][O:4][C:5]1[C:12]([O:13][CH3:14])=[CH:11][CH:10]=[CH:9][C:6]=1[CH2:7][Cl:26]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 81531DiisopropylethylamineHCID 11608100HCID 11608100, compound

Product 1

HCID 12979316HCID 12979316, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

2.34 g (11.8 mmol) of 2-methoxymethoxy-3-methoxybenzyl alcohol was dissolved in 20 ml of diethyl ether, and the resultant solution was added with 1.53 g (11.8, mmol) of N,N-diisopropylethylamine. To the obtained solution was fed dropwise 1.40 g (11.8 mmol) of thionyl chloride and diethyl ether (15 ml) in a manner of spending 15 min. while cooling the solution with ice. The temperature of the resultant mixture was then brought back to a room temperature, and the mixture was stirred all night. The insoluble materials therein are removed by filtration, and the filtrate was condensed under reduced pressure to thereby obtain a crude product of 2-methoxymethoxy-3-methoxybenzyl chloride.

Workup

  1. temperaturewhile cooling the solution with ice
  2. customwas then brought back to a room temperature
  3. customThe insoluble materials therein are removed by filtration
  4. customcondensed under reduced pressure

Sources & evidence

ORD record
ord-80a165b9e075495f898f1bd92bc005f3
Source dataset
uspto-grants-2003_07
Patent number
US06589967B1

Reaction notes

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