Nitrogen → HCID 21997787, compound

HRID 1977131Notes

Reaction equation

HRID 1977131 reaction equation
[C:1]([O:4][C:5]1[C:10]([CH3:11])=[CH:9][C:8]([OH:12])=[C:7]([CH3:13])[C:6]=1[CH3:14])(=[O:3])[CH3:2].[Br:15][CH:16](Br)[CH3:17].C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1.N#N>C(#N)C>[C:1]([O:4][C:5]1[C:10]([CH3:11])=[CH:9][C:8]([O:12][CH2:17][CH2:16][Br:15])=[C:7]([CH3:13])[C:6]=1[CH3:14])(=[O:3])[CH3:2]

Participants

7

Reactant 5

HCID 947NitrogenHCID 112011,1-DibromoethaneHCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 1190244-Hydroxy-2,3,6-trimethylphenyl acetate

Product 1

HCID 21997787HCID 21997787, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-acetoxy-2,3,5-trimethyl phenol (0.94 g, 4.82 mmol), dibromoethane (4 mL), potassium carbonate (0.80 g, 1.2 eq), 18-crown-6 (20 mg) in acetonitrile (15 mL) was stirred and heated at reflux under an atmsophere of N2 for 8 days. After this time the mixture was concentrated at reduced pressure and the residue partitioned between CH2Cl2 and 1M HCl. The organic phase was dried, filtered and concentrated at reduced pressure. The residue was purified by flash chromatography (9:1 ethyl acetate, petroleum spirit). The product was obtained as a white solid (34%) and was recrystallised from petroleum spirit as colourless needles, m.p 59-60° C. 1H NMR (CDCl3) δ6.55 (s, 1H), 4.24 (t, J=6.2 Hz, 2H), 3.64 (t, J=6.2 Hz, 2H), 2.32 (s, 3H), 2.16 (s, 3H), 2.11 (s, 3H), 2.05 (s, 3H).

Workup

  1. temperatureheated
  2. concentrationAfter this time the mixture was concentrated at reduced pressure
  3. customthe residue partitioned between CH2Cl2 and 1M HCl
  4. customThe organic phase was dried
  5. filtrationfiltered
  6. concentrationconcentrated at reduced pressure
  7. customThe residue was purified by flash chromatography (9:1 ethyl acetate, petroleum spirit)

Sources & evidence

ORD record
ord-4de32df15dc545849a28394237a6dc8c
Source dataset
uspto-grants-2001_05
Patent number
US06232314B1

Reaction notes

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