2-Methyl-2-butene → HCID 68282059, compound

HRID 1470489Notes

Reaction equation

HRID 1470489 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[C:8]([CH3:13])[CH:9]=[CH:10][CH:11]=2)[C:6]([CH:14]=[O:15])=[CH:5][CH:4]=1.CC(=CC)C.[O-:21]Cl=O.[Na+]>CC(O)(C)C.O>[CH3:1][O:2][C:3]1[C:12]2[C:7](=[C:8]([CH3:13])[CH:9]=[CH:10][CH:11]=2)[C:6]([C:14]([OH:21])=[O:15])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 866895944-Methoxy-8-methyl-1-naphthaldehyde

Product 1

HCID 68282059HCID 68282059, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

To a solution of 4-methoxy-8-methyl-1-naphthaldehyde (above Step-4 intermediate) (4.4 g, 22 mmol) in tBuOH (50 mL) and 2-methyl-2-butene (23.3 mL, 220 mmol) at 0° C. was added, a solution of NaClO2 (6.0 g, 66 mmol) and NaH2PO4 (9.1 g, 66 mmol) in water (40 mL) drop wise and the reaction mixture was stirred at RT overnight. After completion (TLC), the solvent was evaporated and the residue was basified with 10% NaOH solution and washed with CH2Cl2 (2×50 mL). The aqueous layer was then acidified with 1 N HCl and extracted with EtOAc (4×100 mL). The combined organic layer was washed with water (100 mL), brine (100 mL), dried and filtered. After removal of solvent, the desired compound was obtained (4.5 g, 95%) as an off white solid.

Workup

  1. customAfter completion (TLC), the solvent was evaporated
  2. washwashed with CH2Cl2 (2×50 mL)
  3. extractionextracted with EtOAc (4×100 mL)
  4. washThe combined organic layer was washed with water (100 mL), brine (100 mL)
  5. customdried
  6. filtrationfiltered
  7. customAfter removal of solvent

Sources & evidence

ORD record
ord-9f0c08699cf94637aa8b85c8a490615f
Source dataset
uspto-grants-2015_04
Patent number
US09006442B2

Reaction notes

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