Methyl iodide → HCID 14742757, compound

HRID 1651245Notes

Reaction equation

HRID 1651245 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:15]=[C:14]([OH:16])[C:13]2[C:8](=[CH:9][C:10]([O:17][CH3:18])=[CH:11][CH:12]=2)[C:7]=1[CH2:19][CH2:20][CH2:21][CH3:22])=[O:5])[CH3:2].CI.[C:25](=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:1]([O:3][C:4]([C:6]1[CH:15]=[C:14]([O:16][CH3:25])[C:13]2[C:8](=[CH:9][C:10]([O:17][CH3:18])=[CH:11][CH:12]=2)[C:7]=1[CH2:19][CH2:20][CH2:21][CH3:22])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 14742755HCID 14742755, compound

Product 1

HCID 14742757HCID 14742757, compoundYield 78.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 1-butyl-4-hydroxy-7-methoxy-2-naphthalenecarboxylic acid ethyl ester (6.5 g) and methyl iodide (7 mL) in acetone (65 mL) containing potassium carbonate (5 g) was stirred at room temperature for 64 hours. After the reaction mixture was filtered, the filtrate was concentrated to dryness and the residue was partitioned between dichloromethane (150 mL) and water (100 mL). The dried (MgSO4) organic layer was evaporated and the residual material crystallized from 2-propanol to yield 5.35 g of 1-butyl-4,7-dimethoxy-2-naphthalenecarboxylic acid ethyl ester, mp 44°-45° C. Anal. Calcd for C19H24O3 : C, 72.13; H, 7.64 Found: C, 72.03; H, 7.78

Workup

  1. filtrationAfter the reaction mixture was filtered
  2. concentrationthe filtrate was concentrated to dryness
  3. customthe residue was partitioned between dichloromethane (150 mL) and water (100 mL)
  4. dry with materialThe dried (MgSO4) organic layer
  5. customwas evaporated
  6. customthe residual material crystallized from 2-propanol

Sources & evidence

ORD record
ord-56167f3c233b49028309673183047688
Source dataset
uspto-grants-1990_05
Patent number
US04927838

Reaction notes

Loading…