4-(2-Hydroxyethyl)benzonitrile → HCID 22988443, compound

HRID 987334Notes

Reaction equation

HRID 987334 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[CH:5]([O:14][CH2:15][CH3:16])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)[CH3:2].[C:18]([C:20]1[CH:28]=[CH:27][C:23]([CH2:24][CH2:25]O)=[CH:22][CH:21]=1)#[N:19]>C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:17])[CH:5]([O:14][CH2:15][CH3:16])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][CH2:25][CH2:24][C:23]2[CH:27]=[CH:28][C:20]([C:18]#[N:19])=[CH:21][CH:22]=2)=[CH:11][CH:12]=1)[CH3:2]

Participants

4

Reactant 2

HCID 28008154-(2-Hydroxyethyl)benzonitrileHCID 11791243Ethyl 2-ethoxy-3-(4-hydroxyphenyl)propanoate

Product 1

HCID 22988443HCID 22988443, compoundYield 62.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

3-{4-[2-(4-Cyanophenyl)ethoxy]phenyl}-2-ethoxypropanoic acid ethyl ester was synthesized using the same method as in Example 38(c) using 2-ethoxy-3-(4-hydroxyphenyl) propanoic acid ethyl ester (described in Example 20b) (6.62 g; 27.78 mmole) and p-cyanophenethyl alcohol (2.73 g; 18.52 mmole). The reaction was interrupted after 2 hours. Purification by chromatography on silica gel using first dichloromethane and then petroleum ether:diethyl ether as eluants gave a mixture of product and starting material which was dissolved in ethyl acetate and washed with sodium hydroxide (1 N). The organic phase was washed with water, dried (sodium sulfate), filtered and the solvent as evaporated to give 4.23 g (yield 62%) of 3-{4-[2-(4-cyanophenyl)ethoxy]phenyl}-2-ethoxypropanoic acid ethyl ester.

Workup

  1. custom3-{4-[2-(4-Cyanophenyl)ethoxy]phenyl}-2-ethoxypropanoic acid ethyl ester was synthesized
  2. customPurification by chromatography on silica gel using first dichloromethane
  3. custompetroleum ether:diethyl ether as eluants gave
  4. additiona mixture of product
  5. washwashed with sodium hydroxide (1 N)
  6. washThe organic phase was washed with water
  7. dry with materialdried (sodium sulfate)
  8. filtrationfiltered
  9. customthe solvent as evaporated

Sources & evidence

ORD record
ord-64b1924b441b4ea1b8d0b49943185b50
Source dataset
uspto-grants-2003_10
Patent number
US06630600B1

Reaction notes

Loading…