Acetic Acid → HCID 10657149, compound

HRID 322959Notes

Reaction equation

HRID 322959 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[CH:16]=[CH:15][S:14][CH:13]=2)[CH:7]=[CH:6][C:3]=1[CH:4]=O.[N+:17](CC)([O-])=O.C([O-])(=O)C.[Na+].C(O)(=O)C>O>[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[CH:16]=[CH:15][S:14][CH:13]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:17]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6587NitroethaneHCID 517045Sodium AcetateHCID 10537643HCID 10537643, compound

Product 1

HCID 10657149HCID 10657149, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-hydroxy-4-(3-thienylmethoxy)benzaldehyde (7.7 g), nitroethane (4.74 mL), sodium acetate (5.4 g) and glacial acetic acid (6.6 mL) is heated at reflux for 14 hours. The mixture is then cooled, diluted with water (50 mL) and extracted with ethyl acetate (3×50 mL). The combined organic extracts are washed with saturated aqueous sodium bicarbonate solution (3×50 mL), dried over magnesium sulphate, and concentrated in vacuo. The resulting residue is subjected to flash chromatography on silica gel, eluting with a mixture of ethyl acetate and pentane (3:7 v/v), to give 2-hydroxy-4-(3-thienylmethoxy)benzonitrile (7.6 g), in the form of a pale yellow solid.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 14 hours
  3. temperatureThe mixture is then cooled
  4. extractionextracted with ethyl acetate (3×50 mL)
  5. washThe combined organic extracts are washed with saturated aqueous sodium bicarbonate solution (3×50 mL)
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated in vacuo
  8. washeluting with a mixture of ethyl acetate and pentane (3:7 v/v)

Sources & evidence

ORD record
ord-d5e79df5a6704ccfa8e8c1028b3e4732
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

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