Water → HCID 10016975, compound

HRID 654675Notes

Reaction equation

HRID 654675 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[CH2:12][CH2:13][CH3:14])[C:5]([CH:15]=[O:16])=[CH:4][C:3]=1[O:17][CH3:18].[H-].[Na+].[CH3:21][O:22][CH2:23]Cl.O>CN(C)C=O>[CH3:18][O:17][C:3]1[CH:4]=[C:5]([CH:15]=[O:16])[C:6]2[C:11]([C:2]=1[O:1][CH2:21][O:22][CH3:23])=[C:10]([CH2:12][CH2:13][CH3:14])[CH:9]=[CH:8][CH:7]=2

Participants

6

Reactant 4

HCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 10243542HCID 10243542, compound

Product 1

HCID 10016975HCID 10016975, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
10 °C

Procedure

322 g of 4-hydroxy-3-methoxy-5-propyl-1-naphthalenecarbaldehyde was dissolved in 1.3 liters of N,N-dimethylformamide and cooled to 10° C. 63.3 g of 60% sodium hydride was added to the solution at 30° C. or below and agitated for 20 minutes. The reaction solution was cooled to 5° C., to which 190 ml of chloromethyl methyl ether was added. After agitation at room temperature for 2 hours, the solution was poured into iced water and extracted with ethyl acetate. The resultant organic phase was washed with a saturated saline solution, after which it was dried with anhydrous magnesium sulfate and concentrated under reduced pressure. The resultant residue was purified by silica gel column chromatography (10% ethyl acetate/hexane) to obtain 294.5 g of the captioned compound as a brown oily substance.

Workup

  1. additionwas added
  2. waitAfter agitation at room temperature for 2 hours
  3. extractionextracted with ethyl acetate
  4. washThe resultant organic phase was washed with a saturated saline solution
  5. dry with materialafter which it was dried with anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resultant residue was purified by silica gel column chromatography (10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-e06e09360d9248d89ebd800acdde7953
Source dataset
uspto-grants-1992_07
Patent number
US05134111

Reaction notes

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