Dimethyl Sulfoxide → 2-Heptyloxy-4-iodobenzaldehyde

HRID 1171432Notes

Reaction equation

HRID 1171432 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH2:11]([O:18][C:19]1[CH:24]=[C:23]([I:25])[CH:22]=[CH:21][C:20]=1[CH2:26][OH:27])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].C(N(CC)CC)C>ClCCl.O>[CH2:11]([O:18][C:19]1[CH:24]=[C:23]([I:25])[CH:22]=[CH:21][C:20]=1[CH:26]=[O:27])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 68768142(2-Heptyloxy-4-iodophenyl)methanol

Product 1

HCID 860544942-Heptyloxy-4-iodobenzaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Procedure

A solution of dimethyl sulfoxide (DMSO) (41.4 mmol, 3 ml) in dichloromethane (10 ml) is added to a solution of 1.8 ml of oxalyl chloride (20.7 mmol) in 55 ml of dichloromethane, dropwise, at −78° C. After stirring for 15 minutes, a solution of (2-heptyloxy-4-iodophenyl)methanol obtained in Step b (6.55 g, 18.8 mmol) in 25 ml of dichloromethane is added dropwise. After stirring for 20 minutes, 14 ml of triethylamine are added. After stirring for 2 hours, the reaction medium is hydrolysed by addition of water. The desired product is extracted by addition of ethyl acetate. The organic phase is washed with water, dried with magnesium sulfate and concentrated using a rotary evaporator. After evaporation of the solvents, 6.49 g (100%) of the expected compound are recovered in the form of a yellow solid.

Workup

  1. customat −78° C
  2. stirringAfter stirring for 20 minutes
  3. stirringAfter stirring for 2 hours
  4. extractionThe desired product is extracted by addition of ethyl acetate
  5. washThe organic phase is washed with water
  6. dry with materialdried with magnesium sulfate
  7. concentrationconcentrated
  8. customa rotary evaporator
  9. customAfter evaporation of the solvents, 6.49 g (100%) of the expected compound
  10. customare recovered in the form of a yellow solid

Sources & evidence

ORD record
ord-98427741d4fd48dd8ff517848ac386b8
Source dataset
uspto-grants-2010_11
Patent number
US07829588B2

Reaction notes

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