3-Chloro-1,2-propanediol → HC Orange 3

HRID 1583876Notes

Reaction equation

HRID 1583876 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([OH:14])[CH:7]=[CH:8][C:9]=1[NH:10][CH2:11][CH2:12][OH:13])([O-:3])=[O:2].Cl[CH2:16][CH:17]([OH:20])[CH2:18][OH:19]>C(=O)([O-])[O-].[Na+].[Na+]>[OH:20][CH:17]([CH2:18][OH:19])[CH2:16][O:14][C:6]1[CH:7]=[CH:8][C:9]([NH:10][CH2:11][CH2:12][OH:13])=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1

Participants

4

Reactant 2

HCID 72903-Chloro-1,2-propanediolHCID 54881024-((2-Hydroxyethyl)amino)-3-nitrophenol

Product 1

HCID 21909542HC Orange 3

Reagents, catalysts & solvents 1

HCID 10340Sodium CarbonateSolvent

Conditions

Temperature
90 °C

Procedure

0.2 mol (39.6 g) of 3-nitro-4-[N-(β-hydroxyethyl)-amino]-phenol is dissolved in 125 ml of 2N sodium carbonate solution. 0.25 mol (27.5 g) of 1-chloropropane-2,3-diol is added to this solution, heated beforehand to about 90° C. Heating is maintained for a further 2 hours. After cooling, the reaction medium is extracted with ethyl acetate. After the solvent has been evaporated off to dryness, 29 g of the desired product are obtained in the form of orange crystals.

Workup

  1. temperatureHeating
  2. temperatureis maintained for a further 2 hours
  3. temperatureAfter cooling
  4. extractionthe reaction medium is extracted with ethyl acetate
  5. customAfter the solvent has been evaporated off to dryness, 29 g of the desired product
  6. customare obtained in the form of orange crystals

Sources & evidence

ORD record
ord-c356e852c6524be9a87bf38b8dede37e
Source dataset
uspto-grants-1985_11
Patent number
US04555247

Reaction notes

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