Trimethylamine → Methyl 3-cyano-4-hydroxybenzoate

HRID 222918Notes

Reaction equation

HRID 222918 reaction equation
CC(OC(OC(OC(C)(C)C)=O)=O)(C)C.[OH:16][C:17]1[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][C:18]=1I.[CH3:28][N:29](C)C.O1CCOCC1>O>[C:28]([C:18]1[CH:19]=[C:20]([CH:25]=[CH:26][C:17]=1[OH:16])[C:21]([O:23][CH3:24])=[O:22])#[N:29]

Participants

6

Reactant 4

HCID 1146TrimethylamineHCID 312751,4-DioxaneHCID 90495Di-tert-butyl dicarbonateHCID 11346465Methyl 4-hydroxy-3-iodobenzoate

Product 1

HCID 11769089Methyl 3-cyano-4-hydroxybenzoateYield 154.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(Boc)2O (44.7 g, 0.21 mol) was added portion-wise over 10 min to a 0° C. solution of compound 2 (42 g, 0.19 mol), trimethyl amine (51.9 mL, 0.37 mol), dioxane (140 mL) and water (56 mL). After another 10 min, the ice bath was removed and the reaction mixture was stirred while warming to room temperature for another 2 hours. The reaction mixture was diluted in ethyl acetate (150 mL) and washed with 0.5 N HCl (200 mL×3). The organic layer was dried over magnesium sulfate, filtered, and the filtrate was concentrated in vacuo giving compound 3 (52 g, yield 97%) which was used directly in the next step.

Workup

  1. customthe ice bath was removed
  2. additionThe reaction mixture was diluted in ethyl acetate (150 mL)
  3. washwashed with 0.5 N HCl (200 mL×3)
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-6efd960d7c3b4d7398aa67fc69bc0130
Source dataset
uspto-grants-2012_06
Patent number
US08207340B2

Reaction notes

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