P-Anisidine → HCID 135727398, compound

HRID 972431Notes

Reaction equation

HRID 972431 reaction equation
[CH2:1]([S:19]([C:21]1[C:22]([OH:31])=[CH:23][C:24]2[C:29]([CH:30]=1)=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[OH-].[Na+].[CH3:34][O:35][C:36]1[CH:41]=[CH:40][C:39]([NH2:42])=[CH:38][CH:37]=1.[N:43]([O-])=O.[Na+]>CO.O1CCCC1.O.C(O)(=O)C>[CH3:34][O:35][C:36]1[CH:41]=[CH:40][C:39]([N:42]=[N:43][C:23]2[C:24]3[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:30]=[C:21]([S:19]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[O:20])[C:22]=2[OH:31])=[CH:38][CH:37]=1

Participants

9

Reactant 4

HCID 7732P-AnisidineHCID 14798Sodium HydroxideHCID 21404070HCID 21404070, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 135727398HCID 135727398, compoundYield 95.3%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent3×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 13.0 g (0.029 mole) 3-octadecanesulfinyl-2-naphthol and 5.0 g sodium hydroxide in 300 ml methanol and 200 ml tetrahydrofuran at 0°-5° C. was added a diazonium salt solution prepared from 3.6 g (0.029 mole) p-anisidine in 40 ml water containing 10 ml concentrated hydrochloric acid and a solution of 2.0 g (0.029 mole) sodium nitrite in 20 ml water. The red mixture was stirred at 5° for one hr. and at room temperature overnight, then cooled and acidified with 20 ml acetic acid in 400 ml water. The mixture was filtered to give 16 g of red solid, which could be recrystallized from ethyl acetate to give a solid, m.p. 108°-110° C.

Workup

  1. filtrationThe mixture was filtered

Sources & evidence

ORD record
ord-84a12a2ec4d64632a4a8841d5d516623
Source dataset
uspto-grants-1977_10
Patent number
US04053312

Reaction notes

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