Hydrochloric Acid → 3-Hydroxy-4-cyclohexylphenylglyoxylic acid

HRID 1112167Notes

Reaction equation

HRID 1112167 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 into 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. extractionextracted with chloroform
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue is crystallized

Sources & evidence

ORD record
ord-a70904c0cf9341f68342d388cbc8d910
Source dataset
uspto-grants-1978_10
Patent number
US04120889

Reaction notes

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