2-Methoxynaphthalene → HCID 11107624, compound

HRID 1649951Notes

Reaction equation

HRID 1649951 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1.[Cl-].[Al+3].[Cl-].[Cl-].[C:17]([O:22]C)(=[O:21])[C:18]([CH3:20])=[O:19]>ClC1C=CC=CC=1Cl>[OH:19][C:18]([C:8]1[CH:7]=[CH:6][C:5]2[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=2)[CH:9]=1)([CH3:20])[C:17]([OH:22])=[O:21]

Participants

5

Reactant 3

HCID 71192-MethoxynaphthaleneHCID 11748Methyl pyruvateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 11107624HCID 11107624, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent2×

Procedure

In 20 ml of o-dichlorobenzene were placed 1.58 g of 2-methoxynaphthalene and 2.93 g of anhydrous aluminum chloride. By dissolving 2.04 g of methyl pyruvate in 5 ml of o-dichlorobenzene, the solution was added dropwise to the above mixture at 7° to 11° C. over 13 minutes while stirring. After stirring the mixture for further 30 minutes, ice-cold water was added thereto and the o-dichlorobenzene layer was separated. After washing with water, the o-dichlorobenzene layer was dried over anhydrous magnesium sulfate. By removing o-dichlorobenzene under reduced pressure, the residue was subjected to the same procedure as in Example 3 to give 0.80 g of 2-hydroxy-2-(6-methoxy-2-naphthyl)propionic acid. Yield: 33%.

Workup

  1. additionthe solution was added dropwise to the above mixture at 7° to 11° C. over 13 minutes
  2. stirringAfter stirring the mixture for further 30 minutes
  3. additionice-cold water was added
  4. customthe o-dichlorobenzene layer was separated
  5. washAfter washing with water
  6. dry with materialthe o-dichlorobenzene layer was dried over anhydrous magnesium sulfate
  7. customBy removing o-dichlorobenzene under reduced pressure

Sources & evidence

ORD record
ord-8910ece9df67423ca344e83c3ab45d2d
Source dataset
uspto-grants-1990_05
Patent number
US04922010

Reaction notes

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