Water → HCID 15414486, compound

HRID 594281Notes

Reaction equation

HRID 594281 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[C:4]=1[CH:5]=[O:6].O.C(Cl)[Cl:15]>>[Cl:15][C:10]1[C:3]([O:2][CH3:1])=[C:4]([C:7]([O:11][CH3:12])=[CH:8][CH:9]=1)[CH:5]=[O:6]

Participants

4

Reactant 3

HCID 962WaterHCID 6344Dichloromethane2×HCID 964042,6-Dimethoxybenzaldehyde

Product 1

HCID 15414486HCID 15414486, compound

Conditions

Temperature
50 °C

Procedure

A solution of commercially available 2,6-dimethoxybenzaldehyde (3.000 g; 18.10 mmol) in DCM (12 ml) was treated dropwise with a solution of sulfuryl dichloride SO2Cl2 (2.437 g; 18.10 mmol) in DCM (9 ml), and the resulting mixture was heated to 50° C., under nitrogen, for 30 min. After cooling to rt, water was added and the separated aq. layer was further extracted with DCM. The mixed organic layers were washed with brine, dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (heptane/AcOEt=3/1) afforded 3-chloro-2,6-dimethoxybenzaldehyde as a colorless solid. LC-MS (conditions A): tR=0.67 min.; [M+H]+: 201.03 g/mol.

Workup

  1. temperatureAfter cooling to rt
  2. extractionthe separated aq. layer was further extracted with DCM
  3. washThe mixed organic layers were washed with brine
  4. dry with materialdried over anh. MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure
  7. customPurification by FC (heptane/AcOEt=3/1)

Sources & evidence

ORD record
ord-a94169762d8648d982d951d5a506ef08
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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