Resorcinol → HCID 14520025, compound

HRID 2072901Notes

Reaction equation

HRID 2072901 reaction equation
Cl([O-])=O.[Na+].[CH3:5][O:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:17][CH3:18])[CH:13]=2)[C:8]=1[CH:19]=[O:20].C1(C=CC=C(O)C=1)[OH:22]>O.C(O)(C)(C)C.O1CCOCC1.C(O)(=O)C>[CH3:5][O:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:17][CH3:18])[CH:13]=2)[C:8]=1[C:19]([OH:22])=[O:20]

Participants

8

Reactant 3

HCID 5054ResorcinolHCID 12583354HCID 12583354, compoundHCID 23668197Sodium Chlorite

Product 1

HCID 14520025HCID 14520025, compoundYield 84%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidCatalystHCID 962WaterSolventHCID 6386tert-ButanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
85 °C

Procedure

A solution of sodium chlorite (15.7 g, 80%, 0.139 mol) in 45 mL of water was added rapidly to a warm solution of 2,6-dimethoxy-1-naphthalenecarboxaldehyde [25.76 g, 0.119 mol, described by N. P. Buu-Hoi et al, J. Chem. Soc., 2776 (1955)], resorcinol (17.8 g, 0.162 mol) and acetic acid (0.25 g) in tert-butanol (115 mL) and p-dioxane (95 mL). The reaction temperature was maintained at about 85° C. for 10 minutes then allowed to cool and the mixture was concentrated under vacuum. The residue was partitioned between 1M KOH and dichloromethane. The phases were separated and the aqueous solution was acidified with 6N HCl and washed three times with dichloromethane. The acidic dichloromethane extracts were combined and washed with water and then with saturated sodium chloride and then dried over Na2SO4. After filtration and concentration, the residue was recrystallized from ethanol-water to give 23.1 g (84% yield) of 2,6-dimethoxy-1-naphthalenecarboxylic acid as an off-white solid, m.p. 153°-155° C.

Workup

  1. temperatureto cool
  2. concentrationthe mixture was concentrated under vacuum
  3. customThe residue was partitioned between 1M KOH and dichloromethane
  4. customThe phases were separated
  5. washwashed three times with dichloromethane
  6. washwashed with water
  7. dry with materialwith saturated sodium chloride and then dried over Na2SO4
  8. filtrationAfter filtration and concentration
  9. customthe residue was recrystallized from ethanol-water

Sources & evidence

ORD record
ord-4da0fc4ba60b4bb8ba8ce7e9f1097a2e
Source dataset
uspto-grants-1990_04
Patent number
US04914243

Reaction notes

Loading…