Hydrochloric Acid → HCID 14676200, compound

HRID 1638800Notes

Reaction equation

HRID 1638800 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:12]([OH:14])=[O:13])[CH2:8][CH2:9]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[CH3:23][O:24][CH2:25][CH2:26]Br.[OH-].[Na+].Cl>CO.O.C(OCC)(=O)C.CN(C)C=O>[CH3:23][O:24][CH2:25][CH2:26][O:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:12]([OH:14])=[O:13])[CH2:8][CH2:9]2)=[CH:4][CH:3]=1

Participants

11

Reactant 6

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 809722-Bromoethyl methyl etherHCID 198411996-Hydroxy-3,4-dihydronaphthalene-2-carboxylic acid

Product 1

HCID 14676200HCID 14676200, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 7-hydroxy-1,2-dihydro-3-naphthoic acid (1 g), potassium carbonate (5 g), potassium iodide (2.5 g), N,N-dimethylformamide (30 ml) and methoxy ethyl bromide (2 ml) is stirred for 12 hours at 100° C. After cooling, water (300 ml) and ethyl acetate (200 ml) are added to the reaction mixture, and the mixture is shaken thoroughly. The organic layer is separated, washed with water, dried and evaporated under reduced pressure. the residue is purified by silica gel column chromatography (hexane:ethyl acetate=4:1-2:1) to give a colorless oily product, which is dissolved in methanol (50 ml). To the solution is added an aqueous solution (10 ml) of sodium hydroxide (2 g). The mixture is left standing for one hour, and then acidified with hydrochloric acid, followed by addition of water (300 ml). The resulting precipitates are collected by filtration and recrystallized from a mixture of methanol and water to give 7-methoxyethoxy-1,2-dihydro-3-naphthoic acid (0.65 g) as colorless needles, m.p. 122°-127° C.

Workup

  1. temperatureAfter cooling
  2. stirringthe mixture is shaken thoroughly
  3. customThe organic layer is separated
  4. washwashed with water
  5. customdried
  6. customevaporated under reduced pressure
  7. customthe residue is purified by silica gel column chromatography (hexane:ethyl acetate=4:1-2:1)
  8. customto give a colorless oily product, which
  9. waitThe mixture is left
  10. waitstanding for one hour
  11. customThe resulting precipitates
  12. filtrationare collected by filtration
  13. customrecrystallized from a mixture of methanol and water

Sources & evidence

ORD record
ord-1955eb7ebc004a58b9752ff488186972
Source dataset
uspto-grants-1989_11
Patent number
US04880809

Reaction notes

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