Water → HCID 17604473, compound

HRID 2426602Notes

Reaction equation

HRID 2426602 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[OH:12])[CH:7]=[O:8])[CH3:2].[CH3:13][S:14](Cl)(=[O:16])=[O:15].O>ClCCl>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:7]=[O:8])[CH:9]=[CH:10][C:11]=1[O:12][S:14]([CH3:13])(=[O:16])=[O:15])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 8467EthylvanillinHCID 31297Methanesulfonyl chloride

Product 1

HCID 17604473HCID 17604473, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-ethoxy-4-hydroxybenzaldehyde (3.0 g, 18.1 mmol, 1.0 equiv) and N,N-dimethylaminopyridine (2.87 g, 23.5 mmol, 1.3 equiv) in dichloromethane (10 mL) under Ar at 0° C. was added methanesulfonyl chloride (1.68 mL, 2.48 g, 21.7 mmol, 1.2 equiv). After the reaction mixture was stirred for 1 h, water (100 mL) was added, the solution extracted with dichloromethane (3×50 mL) and the combined organic phases dried over MgSO4. Removal of the solvent by evaporation under reduced pressure provided the title compound in quantitative yield (4.8 g). 1H NMR (300 MHz, CDCl3): δ1.42 (t, J=7.0 Hz, 3H), 3.19 (s, 3H), 4.14 (q, J=7.0 Hz, 2H), 7.41 (s, 2H), 7.45 (s, 1H), 9.89 (s, 1H). 13C NMR (75 MHz, CDCl3): δ14.53, 38.94, 64.99, 112.20, 124.38, 125.17, 136.01, 142.92, 151.63, 190.65. MS (ISP): 245.2 [M+H]+.

Workup

  1. extractionthe solution extracted with dichloromethane (3×50 mL)
  2. dry with materialthe combined organic phases dried over MgSO4
  3. customRemoval of the solvent
  4. customby evaporation under reduced pressure

Sources & evidence

ORD record
ord-7a9051c818ec4557bf77773773556a80
Source dataset
uspto-grants-2011_06
Patent number
US07968568B2

Reaction notes

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