Potassium Carbonate → 4-(4-(Carbomethoxy)methoxyphenylazo)benzyl alcohol

HRID 526266Notes

Reaction equation

HRID 526266 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]=[N:10][C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)=[CH:5][CH:4]=1.Br[CH2:19][C:20]([O:22][CH3:23])=[O:21].C([O-])([O-])=O.[K+].[K+]>CC(C)=O.CCOC(C)=O>[C:20]([CH2:19][O:17][C:14]1[CH:15]=[CH:16][C:11]([N:10]=[N:9][C:6]2[CH:5]=[CH:4][C:3]([CH2:2][OH:1])=[CH:8][CH:7]=2)=[CH:12][CH:13]=1)([O:22][CH3:23])=[O:21]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 1362366624-{2-[4-(Hydroxymethyl)phenyl]hydrazinylidene}cyclohexa-2,5-dien-1-one

Product 1

HCID 866753864-(4-(Carbomethoxy)methoxyphenylazo)benzyl alcohol

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Compound 1 (0.4 g, 1.75 mmol) and methyl bromoacetate (0.28 g, 1.83 mmol) were dissolved in 40 mL of acetone, and K2CO3 (0.726 mg, 5.26 mmol) was added at room temperature followed by stirring overnight. The reaction mixture was diluted with 100 mL of EtOAc and washed with water (2×50 ml), brine (50 ml), and dried over Mg2SO4. After evaporation of solvents under reduced pressure the residue was purified by silica gel column chromatography (EtOAc:n-hexane 4:6) affording compound 3. Yield: 0.395 g (75%). 1H NMR (400 MHz, DMSO-d6) δ 3.71 (s, 3H, Hg), 4.58 (s, 2H, He), 4.92 (s, 2H, Hf), 5.33 (s, 1H, —OH), 7.10-7.14 (m, 2H, Ha), 7.47-7.49 (m, 2H, Hd), 7.80-7.86 (m, 4H, Hb, Hc). 13C NMR (100 MH, DMSO-d6) δ 52.4 (Cg), 62.9 (Cf), 65.3 (Ce), 115.7, 122.6, 124.8, 127.6, 146.3, 147.1, 151.4, 160.6169.4. HRMS (ESI+) m/z: [M+H]+ calcd for C16H17N2O4 301.1188. Found 301.1176.

Workup

  1. washwashed with water (2×50 ml), brine (50 ml)
  2. dry with materialdried over Mg2SO4
  3. customAfter evaporation of solvents under reduced pressure the residue
  4. customwas purified by silica gel column chromatography (EtOAc:n-hexane 4:6)

Sources & evidence

ORD record
ord-c727e398422d41c7b0c5193d46f10b7d
Source dataset
uspto-grants-2016_05
Patent number
US09345781B2

Reaction notes

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