Hydrochloric Acid → 3-Hydroxy-4-cyclohexylphenylglyoxylic acid

HRID 1902768Notes

Reaction equation

HRID 1902768 reaction equation
N[C:2]1[CH:3]=[C:4]([C:14](=[O:20])[C:15]([O:17]CC)=[O:16])[CH:5]=[CH:6][C:7]=1[CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.Cl.N([O-])=[O:23].[Na+]>O>[OH:23][C:2]1[CH:3]=[C:4]([C:14](=[O:20])[C:15]([OH:17])=[O:16])[CH:5]=[CH:6][C:7]=1[CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 20515218Ethyl 3-amino-4-cyclohexylphenylglyoxylateHCID 23668193Sodium Nitrite

Product 1

HCID 205151473-Hydroxy-4-cyclohexylphenylglyoxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 4.5 g. of ethyl 3-amino-4-cyclohexylphenylglyoxylate suspension in 125 ml. of 80% hydrochloric acid and cooled to 0° C. is added dropwise a solution of 1.2 g. of sodium nitrite in 15 ml. of water. After about 10 min., 200 ml. of 50% hydrochloric acid is added portion wise and stirred for 15 hours. The reaction mixture is then poured onto ice water and extracted with chloroform, dried over sodium sulfate and concentrated in vacuo. The residue is crystallized to obtain 3-hydroxy-4-cyclohexylphenylglyoxylic acid.

Workup

  1. additionis added dropwise a solution of 1.2 g
  2. additionThe reaction mixture is then poured onto ice water
  3. extractionextracted with chloroform
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue is crystallized

Sources & evidence

ORD record
ord-d8c49a7c7d604da28611f64fc6fd84a8
Source dataset
uspto-grants-1982_12
Patent number
US04365093

Reaction notes

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