Potassium Iodide → Methyl 4-[5-(4-cyanophenoxy)-pentoxy]-3-methoxybenzoate

HRID 376064Notes

Reaction equation

HRID 376064 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]Cl.[C:8]([C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1)#[N:9].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[C:25]([O:36][CH3:37])(=[O:35])[C:26]1[CH:34]=[CH:33][C:31]([OH:32])=[C:28]([O:29][CH3:30])[CH:27]=1>C(#N)C>[C:8]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:32][C:31]2[CH:33]=[CH:34][C:26]([C:25]([O:36][CH3:37])=[O:35])=[CH:27][C:28]=2[O:29][CH3:30])=[CH:12][CH:11]=1)#[N:9]

Participants

7

Reactant 5

HCID 4875Potassium IodideHCID 11430Potassium Carbonate2×HCID 130194-CyanophenolHCID 19844Methyl VanillateHCID 960701-Bromo-5-chloropentane

Product 1

HCID 18991794Methyl 4-[5-(4-cyanophenoxy)-pentoxy]-3-methoxybenzoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
82 °C

Procedure

To a solution of 1-bromo-5-chloropentane (3794 g, 20.45 mol) in acetonitrile (38 L) is added 4-cyanophenol (2437 g, 20.45 mol) and powdered powdered potassium carbonate (2827 g, 20.45 mol). This suspension is heated with stirring under nitrogen at 96° C. bath temperature (82° C.-internal) for 20 hours. Additional powdered potassium carbonate (2827 g, 20.45 mol.) is then added to the hot reaction mixture followed by potassium iodide (3397 g, 20.45 mol) and methyl vanillate (3725 g, 20.45 mol). The reaction mixture is heated under nitrogen for another 3 days until TLC shows no intermediate chloro compound present. The bath is removed and stirring stopped. The reaction mixture is filtered hot through a filter crock and into another 20 gallon reactor. The filtrate is stirred and cooled with an ice bath to 10° C. for 3 hours and the product filtered, washed with diethyl ether (4×1 L) and dried in vacuo (50° C., 3 mm Hg) to give methyl 4-[5-(4-cyanophenoxy)-pentoxy]-3-methoxybenzoate, mp 105°-107° C., HPLC indicating a purity of 99.8%.

Workup

  1. temperatureThis suspension is heated
  2. temperatureThe reaction mixture is heated under nitrogen for another 3 days until TLC
  3. customThe bath is removed
  4. stirringstirring
  5. filtrationThe reaction mixture is filtered hot through a filter crock and into another 20 gallon reactor
  6. stirringThe filtrate is stirred
  7. temperaturecooled with an ice bath to 10° C. for 3 hours
  8. filtrationthe product filtered
  9. washwashed with diethyl ether (4×1 L)
  10. customdried in vacuo (50° C., 3 mm Hg)

Sources & evidence

ORD record
ord-95c71026e2ff455a9f072017910bef79
Source dataset
uspto-grants-1996_01
Patent number
US05488160

Reaction notes

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