Hydrochloric Acid → HCID 21526281, compound

HRID 1659076Notes

Reaction equation

HRID 1659076 reaction equation
[OH:1][CH:2]([CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[C:12](N)[CH:11]=1)[C:3]([O:5]CC)=[O:4].Cl.N([O-])=[O:25].[Na+]>O>[OH:1][CH:2]([CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[C:12]([OH:25])[CH:11]=1)[C:3]([OH:5])=[O:4]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 21526381HCID 21526381, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 21526281HCID 21526281, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 4.9 g. of ethyl α-hydroxy-γ-(3-amino-4-cyclohexylphenyl)butyrate 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 α-hydroxy-γ-(3-hydroxy-4-cyclohexylphenyl)butyric 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-8e68fed0e779449093e2cad8150ad095
Source dataset
uspto-grants-1976_06
Patent number
US03966801

Reaction notes

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