Potassium Carbonate → HCID 67464169, compound

HRID 2204208Notes

Reaction equation

HRID 2204208 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([O:12][CH3:13])[CH:3]=1.Br[CH2:15][C:16]#[N:17].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C.O>[C:16]([CH2:15][O:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([O:12][CH3:13])[CH:3]=1)#[N:17]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 12532676Methyl 4-hydroxy-2-methoxybenzoate

Product 1

HCID 67464169HCID 67464169, compoundYield 99%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 4-hydroxy-2-methoxy-benzoate (0.790 g, 4.34 mmol), 2-bromoacetonitrile (361 μL, 5.42 mmol), and potassium carbonate (900 mg, 6.51 mmol) were combined in N,N-dimethylformamide (5 mL). The reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was diluted with 50 mL of ethyl acetate and 25 mL of water. The layers were separated and the water layer was extracted with 50 mL of ethyl acetate. The combined organic layers were washed with a saturated aqueous solution of sodium chloride (2×). The organic layer was then dried over sodium sulfate, filtered, and evaporated to dryness to yield methyl 4-(cyanomethoxy)-2-methoxy-benzoate (99%) as a brown oil. ESI-MS m/z calc 221.1, found 222.1 (M+1)+. Retention time: 1.08 minutes (3 min run).

Workup

  1. customThe layers were separated
  2. extractionthe water layer was extracted with 50 mL of ethyl acetate
  3. washThe combined organic layers were washed with a saturated aqueous solution of sodium chloride (2×)
  4. dry with materialThe organic layer was then dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-7a95c16cd5684fbbb21d69e434471f9c
Source dataset
uspto-grants-2016_06
Patent number
US09365588B2

Reaction notes

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