P-Anisidine → HCID 135727396, compound

HRID 972428Notes

Reaction equation

HRID 972428 reaction equation
[CH2:1]([O:19][C:20]1[C:21]([OH:30])=[CH:22][C:23]2[C:28]([CH:29]=1)=[CH:27][CH:26]=[CH:25][CH:24]=2)[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+].[CH3:33][O:34][C:35]1[CH:40]=[CH:39][C:38]([NH2:41])=[CH:37][CH:36]=1.[N:42]([O-])=O.[Na+]>O.C(O)(=O)C.O1CCCC1.CO>[CH3:33][O:34][C:35]1[CH:40]=[CH:39][C:38]([N:41]=[N:42][C:22]2[C:23]3[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:29]=[C:20]([O: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])[C:21]=2[OH:30])=[CH:37][CH:36]=1

Participants

9

Reactant 4

HCID 7732P-AnisidineHCID 14798Sodium HydroxideHCID 21404103HCID 21404103, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 135727396HCID 135727396, compoundYield 1,481.4%

Reagents, catalysts & solvents 4

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

Procedure

To a mixture of 35 g (0.085 mole) 3-octadecyloxy-2-naphthol, 12 g (0.30 mole) sodium hydroxide, 500 ml methanol, and 1000 ml tetrahydrofuran at 0°-5° was added a diazonium salt solution prepared from 10.5 g (0.085 mole) p-anisidine in 40 ml water containing 20 ml concentrated hydrochloric acid and a solution of 5.9 g (0.005 mole) sodium nitrite in 40 ml water. The mixture was stirred at 0°-5° for 1 hour and at room temperature for 1 hour then acidified with 40 ml acetic acid in 1000 ml water. There was obtained 40.5 g of a red solid, which was recrystallized from ethyl acetate to give red crystals, m.p. 95°-97° C.

Sources & evidence

ORD record
ord-e3a9d810b83e41739c5cb344dd5f44bb
Source dataset
uspto-grants-1977_10
Patent number
US04053312

Reaction notes

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