Methanesulfonyl chloride → HCID 86679518, compound

HRID 1776562Notes

Reaction equation

HRID 1776562 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[CH:8][C:7]=2[OH:14])[CH2:3][CH2:2]1.[CH3:15][S:16](Cl)(=[O:18])=[O:17]>C(Cl)Cl>[CH3:15][S:16]([O:14][C:7]1[CH:8]=[C:9]([CH:10]=[O:11])[CH:12]=[CH:13][C:6]=1[O:5][CH2:4][CH:1]1[CH2:3][CH2:2]1)(=[O:18])=[O:17]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chloride2×HCID 59300255HCID 59300255, compound

Product 1

HCID 86679518HCID 86679518, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(cyclopropylmethoxy)-3-hydroxybenzaldehyde (0.440 g, 2.289 mmol) in DCM (20 m), TEA (0.479 ml, 3.43 mmol) was added followed by methanesulfonyl chloride (0.196 ml, 2.52 mmol), and the mixture was stirred at RT overnight. A second portion of TEA (0.096 ml, 0.687 mmol) and methanesulfonyl chloride (0.054 ml, 0.687 mmol) was added, and the reaction was stirred at RT for additional 3 hours. The mixture was washed with HCl 1N and twice with K2CO3 1N. The organic layer was dried over Na2SO4, and the solvent was removed under vacuum affording 2-(cyclopropylmethoxy)-5-formylphenyl methanesulfonate (0.565 g, 2.090 mmol, 91% yield, MS/ESI+ 270.9 [MH]+). This crude was used for the next step without purification.

Workup

  1. stirringthe reaction was stirred at RT for additional 3 hours
  2. washThe mixture was washed with HCl 1N and twice with K2CO3 1N
  3. dry with materialThe organic layer was dried over Na2SO4
  4. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-f2597a6e21544b25adc4484015a7dbc7
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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