2-Naphthol → HCID 894627, compound

HRID 864968Notes

Reaction equation

HRID 864968 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[OH:11].C(=O)([O-])[O-].[K+].[K+].[N+:18]([C:21]1[CH:22]=[C:23]([CH2:27]Br)[CH:24]=[CH:25][CH:26]=1)([O-:20])=[O:19]>CC(C)=O>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[O:11][CH2:27][C:23]1[CH:22]=[C:21]([N+:18]([O-:20])=[O:19])[CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 86632-NaphtholHCID 11430Potassium CarbonateHCID 77568Benzene, 1-(bromomethyl)-3-nitro-

Product 1

HCID 894627HCID 894627, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A stirred solution of 3.8 grams (0.026 mole) of 2-naphthol and 3.6 grams (0.026 mole) of potassium carbonate in 200 mL of acetone was heated at reflux for about 30 minutes. The reaction mixture was then cooled to ambient temperature, and 5.0 grams (0.023 mole) of 3-nitrophenylmethyl bromide was added. Upon completion of addition, the reaction mixture was stirred at ambient temperature for 30 minutes. The reaction mixture was then warmed to reflux where it stirred for about 18 hours. After this time the reaction mixture was cooled to ambient temperature and filtered. The filtrate was concentrated under reduced pressure to a residue. The residue was partitioned between ethyl acetate and an aqueous solution saturated with sodium bicarbonate. The organic layer was separated and washed with three 50 mL portions of an aqueous solution saturated with sodium bicarbonate and then with one 50 mL portion of an aqueous solution saturated with sodium chloride. The organic layer was dried with magnesium sulfate, filtered, and the filtrate concentrated under reduced pressure to a residue. The residue was crystallized with hexane, yielding about 4.5 grams of 3-(naphth-2-yloxymethyl)nitrobenzene. The NMR spectrum was consistent with the proposed structure.

Workup

  1. temperatureat reflux for about 30 minutes
  2. additionUpon completion of addition
  3. temperatureThe reaction mixture was then warmed
  4. temperatureto reflux where it
  5. stirringstirred for about 18 hours
  6. temperatureAfter this time the reaction mixture was cooled to ambient temperature
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure to a residue
  9. customThe residue was partitioned between ethyl acetate
  10. customThe organic layer was separated
  11. washwashed with three 50 mL portions of an aqueous solution saturated with sodium bicarbonate
  12. dry with materialThe organic layer was dried with magnesium sulfate
  13. filtrationfiltered
  14. concentrationthe filtrate concentrated under reduced pressure to a residue
  15. customThe residue was crystallized with hexane

Sources & evidence

ORD record
ord-774e94ccf0d844218ba88e83d28f2ce1
Source dataset
uspto-grants-1996_10
Patent number
US05565451

Reaction notes

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