2-Methyl-2-butene → HCID 22728132, compound

HRID 2086153Notes

Reaction equation

HRID 2086153 reaction equation
[CH3:1][C:2]1[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[C:15]([CH3:22])[C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([O:13][CH3:14])=[C:9]([CH:12]=1)[CH:10]=[O:11].CC(=CC)C.Cl([O-])=[O:29].[Na+].[O-]S([O-])(=S)=O.[Na+].[Na+]>O1CCCC1.C(O)(C)(C)C.OP([O-])(O)=O.[K+]>[CH3:22][C:15]1[CH:16]=[C:17]([N+:19]([O-:21])=[O:20])[CH:18]=[C:2]([CH3:1])[C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([O:13][CH3:14])=[C:9]([CH:12]=1)[C:10]([OH:29])=[O:11]

Participants

8

Reactant 4

HCID 105532-Methyl-2-buteneHCID 24477Sodium ThiosulfateHCID 22728121HCID 22728121, compoundHCID 23668197Sodium Chlorite

Product 1

HCID 22728132HCID 22728132, compoundYield 111.3%

Reagents, catalysts & solvents 3

HCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolventHCID 516951Monobasic potassium phosphateSolvent

Procedure

To a solution of 5-(2,6-dimethyl-4-nitro-phenoxy)-2-methoxy-benzaldehyde (6.6 g, 21.8 mmol) and 2-methyl-2-butene (23.0 g, 327 mmol) in a mixture of tetrahydrofuran (31 mL) and t-butyl alcohol (210 mL) at room temperature was added dropwise a solution of sodium chlorite (17.7 g, 196 mmol) in KH2PO4 (0.6 M, 254 mL). The resulting mixture was stirred at room temperature for 16 hours, and then saturated aqueous Na2S2O3 (100 mL) was added. The solution was stirred at room temperature for 30 minutes and extracted with ethyl acetate (3 times 300 mL). The combined organic extracts were dried over Na2SO4 and concentrated to afford the title compound (7.7 grams) as a crude product. The product was used in the next step without purification. 1H NMR (400 MHz, CDCl3) δ8.01 (s, 2H), 7.49 (s, 1H), 7.02 (s, 2H), 4.06 (s, 3H), 2.19 (s, 6H). MS (APCI−) Calc: 317.3, Found: 316.3 (M−1).

Workup

  1. stirringThe solution was stirred at room temperature for 30 minutes
  2. extractionextracted with ethyl acetate (3 times 300 mL)
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-210fdccd050c4ef2848f94c369682022
Source dataset
uspto-grants-2004_04
Patent number
US06723744B2

Reaction notes

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