2-Methyl-2-butene → HCID 71185803, compound

HRID 1470510Notes

Reaction equation

HRID 1470510 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10]([CH:12]=[O:13])=[CH:9][CH:8]=[C:7]2[O:14][CH3:15].CC(=CC)C.[O-:21]Cl=O.[Na+]>CC(O)(C)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10]([C:12]([OH:21])=[O:13])=[CH:9][CH:8]=[C:7]2[O:14][CH3:15]

Participants

6

Reactant 3

HCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 86689598HCID 86689598, compound

Product 1

HCID 71185803HCID 71185803, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

To a mixture of 8-chloro-4-methoxy-1-naphthaldehyde (step-3 intermediate) (2.0 g, 9.06 mmol) in tBuOH (20 mL) and 2-methyl-2-butene (14.4 mL, 136.0 mmol) at 0° C. was added a solution of NaClO2 (4.1 g, 45.3 mmol) and NaH2PO4.H2O (6.3 g, 45.3 mmol) in H2O (16 mL) dropwise. The resulting solution was stirred at RT for 24 h. The solvent was evaporated and the crude mixture was basified with 10% NaOH solution and then washed with EtOAc. The aqueous layer was acidified with 1 N HCl and again extracted with EtOAc. The combined organic layer was washed with water, brine, dried (Na2SO4) and filtered. The solvent was evaporated to provide the desired acid as pale yellow solid (1.7 g, 80%).

Workup

  1. customThe solvent was evaporated
  2. washwashed with EtOAc
  3. extractionagain extracted with EtOAc
  4. washThe combined organic layer was washed with water, brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customThe solvent was evaporated

Sources & evidence

ORD record
ord-5d34de04f95f4d37b280def752d7d506
Source dataset
uspto-grants-2015_04
Patent number
US09006442B2

Reaction notes

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