Acetic Acid → Ethyl 3-(4-cyano-3-hydroxyphenyl)propanoate

HRID 1937780Notes

Reaction equation

HRID 1937780 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5][C:4]=1[O:16]C)#[N:2].[C-]#N.[Na+].CC(O)=O>CS(C)=O.O>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5][C:4]=1[OH:16])#[N:2]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 8929Sodium CyanideHCID 22461741Ethyl 3-(4-cyano-3-methoxyphenyl)propionate

Product 1

HCID 9834402Ethyl 3-(4-cyano-3-hydroxyphenyl)propanoate

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of ethyl 3-(4-cyano-3-methoxyphenyl)propionate (3.17 g, 13.6 mmol, 1 equiv) and sodium cyanide (2.00 g, 40.8 mmol, 3.00 equiv) in DMSO (60 mL) was stirred at 140-180° C. for 2 h. After 2.5 hours the reaction mixture was taken up in H2O (300 mL), adjusted to pH 7 with AcOH (2.1 mL), and extracted with Et2O (1×150 mL). The organic layer was washed with H2O (2×50 mL), dried (anh. Na2SO4), and concentrated (75° C.). This yielded 2.05 g (68.8%) of ethyl 4-(4-cyano-3-hydroxyphenyl)propionate as a light yellow crystalline solid: 1H-NMR (CDCl3) 7.42 (1H, d), 7.40 (1H, br s), 6.92 (1H, d), 6.81 (1H, dd), 4.15 (2H, q), 2.94 (2H, dd), 2.64 (2H, dd), 1.25 (3H, t).

Workup

  1. extractionextracted with Et2O (1×150 mL)
  2. washThe organic layer was washed with H2O (2×50 mL)
  3. dry with materialdried (anh. Na2SO4)
  4. concentrationconcentrated (75° C.)

Sources & evidence

ORD record
ord-0be0cba3c0134771b61f78e1ebfd5c3f
Source dataset
uspto-grants-2002_05
Patent number
US06395919B1

Reaction notes

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