Hydrochloric Acid → Methyl 2-heptyloxy-4-iodobenzoate

HRID 1171436Notes

Reaction equation

HRID 1171436 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[I:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]([OH:18])[CH:9]=1.I[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].Cl>CN(C=O)C>[CH2:20]([O:18][C:10]1[CH:9]=[C:8]([I:7])[CH:17]=[CH:16][C:11]=1[C:12]([O:14][CH3:15])=[O:13])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 202741-IodoheptaneHCID 11380407Methyl 4-iodosalicylate

Product 1

HCID 68767792Methyl 2-heptyloxy-4-iodobenzoateYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of caesium carbonate (35.2 g, 108 mmol), methyl 4-iodo-2-hydroxybenzoate (25 g, 90 mmol), iodoheptane (19.2 ml, 117 mmol) in DMF (500 ml) is stirred for 10 hours at room temperature. The organic phase is acidified at room temperature with a 2N hydrochloric acid solution to pH 5. 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 remainder of the iodoheptane by placing the oil obtained under vacuum produced by a rotary vane pump, 33.8 g (100%) of the expected compound are recovered in the form of a brown oil.

Workup

  1. extractionThe desired product is extracted by addition of ethyl acetate
  2. washThe organic phase is washed with water
  3. dry with materialdried with magnesium sulfate
  4. concentrationconcentrated
  5. customa rotary evaporator
  6. customAfter evaporation of the remainder of the iodoheptane
  7. customobtained under vacuum

Sources & evidence

ORD record
ord-0e218b050248476fb30901644d11cf9b
Source dataset
uspto-grants-2010_11
Patent number
US07829588B2

Reaction notes

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