Hydrochloric Acid → HCID 15182122, compound

HRID 394671Notes

Reaction equation

HRID 394671 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[O:11]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[O:14][CH:13]=[C:12]1[CH2:21][OH:22].C(N(CC)CC)C.Cl>ClCCl>[O:11]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[O:14][CH:13]=[C:12]1[CH:21]=[O:22]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 108447491,4-Benzodioxin-2-methanol

Product 1

HCID 15182122HCID 15182122, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1.2 ml (14 mmol) of oxalyl chloride in 30 ml of anhydrous dichloromethane is cooled to −60° C. under an inert atmosphere; 2 ml (28 mmol) of anhydrous dimethyl sulphoxide are then added to the medium. After 5 minutes of stirring, 1.53 g (9.33 mmol) of the alcohol obtained in Step A in 15 ml of dichloromethane are slowly added to the solution. 15 minutes later, 6.5 ml (47 mmol) of triethylamine are added to the medium. After returning to ambient temperature, the solution is acidified with a hydrochloric acid solution (1N); the aqueous phase is then extracted with dichloromethane. The organic phases, dried over magnesium sulphate and then filtered, are concentrated in vacuo. The title aldehyde is obtained pure in the form of a white solid after passage over a silica column (eluant: AcOEt/PE: 10/90).

Workup

  1. customAfter returning to ambient temperature
  2. extractionthe aqueous phase is then extracted with dichloromethane
  3. dry with materialThe organic phases, dried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationare concentrated in vacuo

Sources & evidence

ORD record
ord-9fbfa1d0a2b54e45b41503ac46c6d375
Source dataset
uspto-grants-2003_08
Patent number
US06602903B2

Reaction notes

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