2-Methoxynaphthalene → HCID 11150732, compound

HRID 1886255Notes

Reaction equation

HRID 1886255 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH3:5][O:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=1.[Cl-].[C:18]([O:27][CH3:28])(=[O:26])[CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O-])=[O:24].C(Cl)(=O)C(Cl)=O.C(OC)(=O)CCCCC([O-])=O>[N+](C1C=CC=CC=1)([O-])=O.C(Cl)Cl>[CH3:5][O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH:13]=[C:12]([C:23](=[O:24])[CH2:22][CH2:21][CH2:20][CH2:19][C:18]([O:27][CH3:28])=[O:26])[CH:11]=[CH:10]2

Participants

8

Reactant 5

HCID 71192-MethoxynaphthaleneHCID 65578Oxalyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 6994472Methyl adipateHCID 19877562HCID 19877562, compound

Product 1

HCID 11150732HCID 11150732, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7416NitrobenzeneSolvent

Procedure

Into a solution of 6.32 g (47.4 mmol) of anhydrous aluminum chloride in 60 ml of dry nitrobenzene was added 5.03 g (31.7 mmol) of 2-methoxynaphthalene chilled with an ice bath, followed by stirring. Subsequently, under an ice bath, monomethyl adipate chloride (synthesized by adding 5.0 ml (57.3 mmol) of oxalyl chloride under an ice bath to a solution of 5.85 ml (39.5 mmol) monomethyl adipate in 50 ml of dry methylene chloride) to carry out the reaction for 6 hours, and evaporating methylene chloride and excessive oxalyl chloride under a reduced pressure) was gradually added, and the reaction was carried out at 0° C. to room temperature overnight (for 15 hours). The reaction mixture was poured into ice-water, extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate. After evaporation of the organic solvent and nitrobenzene under a reduced pressure, the desired product was obtained by silica gel chromatography. Yield: 3.82 g (40%).

Workup

  1. temperaturechilled with an ice bath
  2. customthe reaction for 6 hours
  3. customevaporating methylene chloride and excessive oxalyl chloride under a reduced pressure)
  4. additionwas gradually added
  5. custom(for 15 hours)
  6. additionThe reaction mixture was poured into ice-water
  7. extractionextracted with ethyl acetate
  8. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  9. customAfter evaporation of the organic solvent and nitrobenzene under a reduced pressure

Sources & evidence

ORD record
ord-49e4bdc18f9d4ffc94b775449addc6a0
Source dataset
uspto-grants-1992_09
Patent number
US05149859

Reaction notes

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