Dimethyl Sulfoxide → 2,6-Dichloro-4-nitrobenzaldehyde

HRID 746040

Reaction equation

HRID 746040 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[Cl:11][C:12]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[C:16]([Cl:23])[C:13]=1[CH2:14][OH:15].C(N(CC)CC)C>ClCCl.O>[Cl:11][C:12]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[C:16]([Cl:23])[C:13]=1[CH:14]=[O:15]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 23311409(2,6-Dichloro-4-nitrophenyl)methanol

Product 1

HCID 218388352,6-Dichloro-4-nitrobenzaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Procedure

A solution of dimethyl sulphoxide (1.2 cm3) in dichloromethane (5 cm3) was added dropwise to a stirred solution of oxalyl chloride (0.7 cm3, 8.0 mmol) in dichloromethane (12 cm3) at -60° C. under nitrogen. After 10 mins at -60° C. a solution of 2,6-dichloro-4-nitrobenzylalcohol (1.53 g, 6.9 mmol) in dichloromethane (10 cm3) was added dropwise and the stirred mixture kept at -60° C. for 0.5 h. Triethylamine (4.6 cm3, 33 mmol) was then added and the mixture was allowed to warm to room temperature at which stage water (35 cm3) was added. The heterogeneous mixture was separated and the aqueous phase extracted with dichloromethane (35 cm3). The combined organic fractions were extracted with hydrochloric acid (2M, 60 cm3), then water (60 cm3), saturated sodium carbonate solution (60 cm 3), and finally water (60 cm3) then dried and evaporated under reduced pressure to give 2,6-dichloro-4-nitrobenzaldehyde as a pure oil which slowly solidified.

Workup

  1. additionwas added
  2. customThe heterogeneous mixture was separated
  3. extractionthe aqueous phase extracted with dichloromethane (35 cm3)
  4. extractionThe combined organic fractions were extracted with hydrochloric acid (2M, 60 cm3)
  5. dry with materialwater (60 cm3), saturated sodium carbonate solution (60 cm 3), and finally water (60 cm3) then dried
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-5c34ea4784db4b95bab3b91e2d6a1307
Source dataset
uspto-grants-1986_07
Patent number
US04602041

Linked notes

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