Chloroethane → 6-Hydroxynaphthalene-2-sulfonic acid

HRID 1759514Notes

Reaction equation

HRID 1759514 reaction equation
[NH:1]([C:5]1[C:14]2[C:9](=[CH:10][C:11]([S:15]([OH:18])(=[O:17])=[O:16])=[CH:12][CH:13]=2)[CH:8]=[CH:7][C:6]=1[OH:19])[C:2]([CH3:4])=[O:3].C(=O)([O-])[O-].[K+].[K+].[OH-].[K+].[CH2:28](Cl)[CH3:29]>O.CO>[NH2:1][C:5]1[C:14]2[C:9](=[CH:10][C:11]([S:15]([OH:18])(=[O:16])=[O:17])=[CH:12][CH:13]=2)[CH:8]=[CH:7][C:6]=1[O:19][CH2:28][CH3:29].[NH:1]([C:5]1[C:14]2[C:9](=[CH:10][C:11]([S:15]([OH:18])(=[O:16])=[O:17])=[CH:12][CH:13]=2)[CH:8]=[CH:7][C:6]=1[OH:19])[C:2]([CH3:4])=[O:3].[OH:19][C:6]1[CH:7]=[CH:8][C:9]2[C:14](=[CH:13][CH:12]=[C:11]([S:15]([OH:18])(=[O:16])=[O:17])[CH:10]=2)[CH:5]=1

Participants

9

Reactant 4

HCID 6337ChloroethaneHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 133359N-Acetyl-(1-amino-2-naphthol-6-sulfonic acid)

Product 3

HCID 71176-Hydroxynaphthalene-2-sulfonic acidHCID 133359N-Acetyl-(1-amino-2-naphthol-6-sulfonic acid)HCID 2221662-Naphthalenesulfonic acid, 5-amino-6-ethoxy-

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

12.5 parts of 1-acetamino-2-hydroxy-naphthalene-6-sulphonic acid (67.5% pure=8.5 parts of 100% pure), prepared according to Example 4, and 4.2 parts of potassium carbonate are suspended in a mixture of 47.4 parts by weight of methanol and 9.0 parts by weight of water in an autoclave. After heating the autoclave, 6.2 parts of 25% strength potassium hydroxide solution and 5.8 parts of ethyl chloride are simultaneously metered in at 120° C. The reaction mixture is worked up analogously to Example 12. 87% of theory of 1-amino-2-ethoxy-naphthalene-6-sulphonic acid, relative to 1-acetamino-2-hydroxy-naphthalene-6-sulphonic acid, or 67.8% of theory, relative to 2-hydroxy-naphthalene-6-sulphonic acid, are obtained.

Workup

  1. customare simultaneously metered in at 120° C

Sources & evidence

ORD record
ord-d9d6743fe5a84dddb35021e780b3007d
Source dataset
uspto-grants-1982_07
Patent number
US04341719

Reaction notes

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