Potassium Carbonate → 5-(Chloromethyl)-1,2,3-trimethoxybenzene

HRID 1460158Notes

Reaction equation

HRID 1460158 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:13][CH3:14])[C:10]=1[O:11][CH3:12])[CH2:6]O.S(Cl)([Cl:17])=O.C(=O)([O-])[O-].[K+].[K+]>C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:13][CH3:14])[C:10]=1[O:11][CH3:12])[CH2:6][Cl:17]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 24386Thionyl ChlorideHCID 774493,4,5-Trimethoxybenzyl alcohol

Product 1

HCID 774485-(Chloromethyl)-1,2,3-trimethoxybenzene

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

In 40 ml of benzene was dissolved 10 g of 3,4,5-trimethoxybenzyl alcohol. To the resulting solution was dropwise added under chilling with ice 10 ml of benzene solution containing 7.6 g of thionyl chloride. After the addition was complete, the mixture was stirred at room temperature for 15 min. The reaction solution was poured into a chilled aqueous potassium carbonate, and a separated benzene portion was collected. The benzene portion was washed with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and placed under reduced pressure to distill off the solvent. The desired compound was obtained as a yellow solid (yield: 11.0 g).

Workup

  1. additionTo the resulting solution was dropwise added
  2. additionAfter the addition
  3. customa separated benzene portion was collected
  4. washThe benzene portion was washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationto distill off the solvent

Sources & evidence

ORD record
ord-f8dadac5743049fab0bd34e3615ffa01
Source dataset
uspto-grants-1991_12
Patent number
US05070089

Reaction notes

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