Hydrochloric Acid → HCID 15380895, compound

HRID 581065Notes

Reaction equation

HRID 581065 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH2:12][C:13]1[C:22]2[O:21][CH:20]=[CH:19][O:18][C:17]=2[CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C.Cl>ClCCl>[CH:12]([C:13]1[C:22]2[O:21][CH:20]=[CH:19][O:18][C:17]=2[CH:16]=[CH:15][CH:14]=1)=[O:11]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 15380894HCID 15380894, compound

Product 1

HCID 15380895HCID 15380895, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1.27 g (10.05 mmol) of oxalyl chloride in 30 ml of anhydrous dichloromethane is cooled to -60° C. and then 1.57 g (20.1 mmol) of dimethyl sulphoxide are added to the mixture. After 5 minutes' stirring under an inert atmosphere, 1.1 g of 5-hydroxymethyl-1,4-benzodioxin (6.7 mmol) dissolved in 15 ml of dichloromethane are slowly added to the mixture which is then stirred for a further 15 minutes. 4.66 ml (33.5 mmol) of triethylamine are subsequently added to the mixture which is then allowed to return to room temperature. The solution is then acidified with a 1N hydrochloric acid solution and the aqueous phase is subsequently extracted with dichloromethane. The organic phase, dried over magnesium sulphate and then filtered, is concentrated under reduced pressure. The title aldehyde is obtained pure in the form of a yellow solid after passage over a silica column (eluant:AcOEt/PE:10/90).

Workup

  1. additionare slowly added to the mixture which
  2. customto return to room temperature
  3. extractionthe aqueous phase is subsequently extracted with dichloromethane
  4. dry with materialThe organic phase, dried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationis concentrated under reduced pressure

Sources & evidence

ORD record
ord-5333d6205aa6405995b3a8d11a2b2aed
Source dataset
uspto-grants-1999_07
Patent number
US05919814

Reaction notes

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