Water → Methyl 4-(cyanomethyl)benzoate

HRID 411592

Reaction equation

HRID 411592 reaction equation
[C-:1]#[N:2].[Na+].Br[CH2:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][CH:7]=1.O>C1COCC1.CN(C=O)C>[C:10]([C:9]1[CH:14]=[CH:15][C:6]([CH2:5][C:1]#[N:2])=[CH:7][CH:8]=1)([O:12][CH3:13])=[O:11]

Participants

6

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 256687Methyl 4-(bromomethyl)benzoate

Product 1

HCID 848548Methyl 4-(cyanomethyl)benzoateYield 76%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Part A: To a stirred solution of 7.5 g(153 mmol) sodium cyanide in 75 mL of THF was added 40 mL of DMF followed by 11.5 g(50.2 mmol) of of methyl 4-(bromomethyl)benzoate in 30 mL of DMF over 10 min. The solution was stirred 18 and treated with 100 mL water. The mixture was filtered, rinsed with water, and air-dried briefly to give 6.7 g (76%) of 4-(carbomethoxy)phenylacetonitrile as a white solid. 1H NMR (300 MHz, DMSO) δ 7.95(d, 2H, J=8.4 Hz); 7.47(d, 2H, J=8.5 Hz); 4.14(s, 2H); 3.82(s, 3H). Part B: The above nitrile ester was stirred with 120 mL of 6 N aq. HCl for 18 h at reflux and then cooled. The mixture was diluted with 160 mL water and then filtered. The white solid was rinsed with water, air-dried briefly, and placed in a vacuum oven at 75° C. for 1 h. This affords 6.89 g (100%) of 4-(carboxy)phenylacetic acid. 1H NMR (300 MHz, DMSO) δ 7.92(d, 2H, J=8.5 Hz); 7.49(d, 2H, J=8.4 Hz); 3.63(s, 2H)

Workup

  1. filtrationThe mixture was filtered
  2. washrinsed with water
  3. customair-dried briefly

Sources & evidence

ORD record
ord-7c83edd417384124b4529fe37d55a4d4
Source dataset
uspto-grants-2003_05
Patent number
US06559152B2

Linked notes

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