Hydrochloric Acid → 2-Heptyloxy-4-iodobenzaldehyde

HRID 1171442Notes

Reaction equation

HRID 1171442 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].Cl>ClCCl>[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

6

Reactant 4

HCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 68768142(2-Heptyloxy-4-iodophenyl)methanol

Product 1

HCID 860544942-Heptyloxy-4-iodobenzaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of dimethyl sulfoxide (3 ml, 41.4 mmol) in dichloromethane is added to a solution of oxalyl chloride (20.7 mmol, 1.8 ml) in dichloromethane (55 ml). A solution of (2-heptyloxy-4-iodophenyl)methanol (6.55 g, 18.8 mmol) in 25 ml of dichloromethane is added dropwise to the solution previously obtained, at −78° C. The mixture is stirred until the temperature returns to room temperature. The organic phase is acidified with a 2N hydrochloric acid solution. 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. 6.5 g (100%) of the expected compound are recovered in the form of a yellow solid.

Workup

  1. custompreviously obtained, at −78° C
  2. extractionThe desired product is extracted by addition of ethyl acetate
  3. washThe organic phase is washed with water
  4. dry with materialdried with magnesium sulfate
  5. concentrationconcentrated
  6. customa rotary evaporator
  7. custom6.5 g (100%) of the expected compound are recovered in the form of a yellow solid

Sources & evidence

ORD record
ord-cb547eed9e454edfb53e66fa6ab30b5e
Source dataset
uspto-grants-2010_11
Patent number
US07829588B2

Reaction notes

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