Hydrochloric Acid → 4-((4-(Hydroxymethyl)phenyl)diazenyl)-3-methoxyphenol

HRID 526265Notes

Reaction equation

HRID 526265 reaction equation
NC1C=CC(CO)=CC=1.N([O-])=O.[Na+].Cl.[CH3:15][O:16][C:17]1[CH:18]=[C:19]([OH:23])[CH:20]=[CH:21][CH:22]=1.CC([O-])=O.[Na+].[OH:29][CH2:30][C:31]1[CH:36]=[CH:35][C:34]([N:37]=[N:38]C2C=CC(O)=CC=2)=[CH:33][CH:32]=1>CCO.O.CCO>[OH:29][CH2:30][C:31]1[CH:36]=[CH:35][C:34]([N:37]=[N:38][C:22]2[CH:21]=[CH:20][C:19]([OH:23])=[CH:18][C:17]=2[O:16][CH3:15])=[CH:33][CH:32]=1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 90073-MethoxyphenolHCID 693314-Aminobenzyl alcoholHCID 517045Sodium AcetateHCID 23668193Sodium NitriteHCID 1362366624-{2-[4-(Hydroxymethyl)phenyl]hydrazinylidene}cyclohexa-2,5-dien-1-one

Product 1

HCID 1364132044-((4-(Hydroxymethyl)phenyl)diazenyl)-3-methoxyphenol

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 19096565Water ethanolSolvent

Conditions

Temperature
0 °C

Procedure

4-Aminobenzyl alcohol (0.275 g, 2.24 mmol) and NaNO2 (0.16 g, 2.35 mmol) were dissolved in 7.5 mL EtOH:water (1.5:1) and added to 2 N HCl solution (4.5 mL) and reaction mixture stirred at 0° C. for 1 hour. 3-methoxyphenol (0.25 g, 2.01 mmol) in EtOH was added, followed by addition of NaOAc (0.15 g) at 0° C. and remaining procedure followed as described for compound 1 to obtain compound 2. Yield: 0.435 g (84%). 1H NMR (500 MHz, CD3SOCD3) δ 3.34 (bs, 4H, OMe, —OH), 4.55 (bs, 2H, Hf), 5.31 (s, 1H, phenol-OH), 6.43-6.46 (m, 1H, Hb), 6.57-6.60 (m, 1H, He), 7.44-7.48 (m, 2H, He), 7.53-7.57 (m, 1H, Ha), 7.69-7.74 (m, 2H, Hd). 13C NMR (125 MHz, CD3SOCD3) δ 55.7 (OMe), 62.5 (Cf), 99.9 (Cc), 107.9 (Cb), 117.4 (Ci), 121.9 (Cd), 127.0 (Ce), 134.8 (Ca), 144.7 (Ck), 151.5 (Cj), 158.9 (Ch), 162.6 (Cg). ESI-MS: [M+H]+ C14H15N2O3 calcd 259.1083, obsd 259.10.

Sources & evidence

ORD record
ord-4b090dbb74a140a3a20459d90a93ef40
Source dataset
uspto-grants-2016_05
Patent number
US09345781B2

Reaction notes

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