1,5-Dihydroxynaphthalene → HCID 22596463, compound

HRID 1760655Notes

Reaction equation

HRID 1760655 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[C:7]([OH:12])[CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.[CH3:13][O:14][CH:15]([O:18][CH3:19])[CH2:16]Cl>CC(N(C)C)=O>[CH3:13][O:14][CH:15]([O:18][CH3:19])[CH2:16][O:1][C:2]1[C:11]2[C:6](=[C:7]([O:12][CH2:16][CH:15]([O:18][CH3:19])[O:14][CH3:13])[CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 67491,5-DihydroxynaphthaleneHCID 609862-Chloro-1,1-dimethoxyethane

Product 1

HCID 22596463HCID 22596463, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
80 °C

Procedure

72 g (0.45 mol) 1,5-dihydroxynaphthalene are dissolved in 400 ml DMAc while heating in a three-necked flask fitted with a dropping funnel, internal thermometer, column and distillation cap. Then, at an internal temperature of 110-130° C., 178 g (1.1 mol) of a 30% solution of sodium methanolate in methanol are added dropwise and the resulting methanol is distilled off continuously via the column. When all the methanol has been transferred, 136 g (1.1 mol) chloracetaldehyde dimethylacetal is added in one portion, and the reaction is allowed to continue for approximately 3 hours at 130° C. Following this, the reaction mixture is cooled to 80° C., filtered while still warm, and the filtrate is poured onto 1000 g iced water to which 15 g NaOH have been added. The precipitate is filtered off, washed thoroughly with water and then dried under vacuum at 60° C. A yield of 80 g (53%) 1,5-bis-(2,2′-dimethoxyethoxy)naphthalene is obtained. Melting point: 117° C.; IR (KBr): 1273 cm−1 (ether); MS: m/e=336 (M+), 304, 273, 241, 215, 197, 185, 171, 160, 115, 89, 75, 59, 43.

Workup

  1. temperaturewhile heating in a three-necked flask
  2. customfitted with a dropping funnel
  3. distillationinternal thermometer, column and distillation
  4. customcap
  5. additionThen, at an internal temperature of 110-130° C., 178 g (1.1 mol) of a 30% solution of sodium methanolate in methanol are added dropwise
  6. distillationthe resulting methanol is distilled off continuously via the column
  7. filtrationfiltered
  8. temperaturewhile still warm
  9. additionthe filtrate is poured onto 1000 g iced water to which 15 g NaOH
  10. additionhave been added
  11. filtrationThe precipitate is filtered off
  12. washwashed thoroughly with water
  13. customdried under vacuum at 60° C

Sources & evidence

ORD record
ord-4f6272bd656445ca9f9f357cceb6c3bc
Source dataset
uspto-grants-2005_01
Patent number
US06844375B2

Reaction notes

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