Hydrochloric Acid → 1-Naphthol

HRID 1602203Notes

Reaction equation

HRID 1602203 reaction equation
[N+]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][C:11]2=[O:14])=[CH:6][CH:5]=1)([O-])=O.[BH4-].[Na+].Cl>C(O)C.O>[C:11]1([OH:14])[C:12]2[C:7](=[CH:6][CH:5]=[CH:4][CH:13]=2)[CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 384457-Nitro-1-tetraloneHCID 4311764Sodium borohydride

Product 1

HCID 70051-NaphtholYield 123.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a slurry of 2.88 g (15 mmol) of 7-nitro-1-tetralone in 60 mL absolute ethanol was added 0.58 g (15 mmol) of sodium borohydride. The reaction mixture was then stirred at room temperature for 2 hours. The resulting mixture was then rotaevaporated to dryness and the residue obtained was suspended in 100 mL of water. 3 N hydrochloric acid was added dropwise until the reaction mixture had pH 7. The suspension obtained was then extracted with five 50 mL portions of ethyl ether and the combined ether layer was washed once with 100 mL water. The ether layer was dried over anhydrous sodium sulfate, filtered and rotaevaporated to give an off-white residue which was recrystallized from a 1:1 mixture of absolute ethanol and water to yield 2.68 g (92%) of the napthalenol; mp 112-113° C.; IR (KBr): 3300; 1H NMR: δ1.73-2.26 (4H, m), 2.29 (1H, s), 2.78-2.91 (2H, m), 4.83(1H, m), 7.24 (1H, d, J=8.1), 8.00-8.04 (1H, dd, J=8.1, 2.4), 8.35(1H, d, J=2.4),; 13C NMR: δ19.2, 29.9, 32.5, 68.3, 122.7, 124.1, 130.3, 140.9, 145.4.

Workup

  1. customthe residue obtained
  2. customThe suspension obtained
  3. extractionwas then extracted with five 50 mL portions of ethyl ether
  4. washthe combined ether layer was washed once with 100 mL water
  5. dry with materialThe ether layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customto give an off-white residue which
  8. customwas recrystallized from a 1:1 mixture of absolute ethanol and water

Sources & evidence

ORD record
ord-b176c7c469f94e56b3004eabd139cb55
Source dataset
uspto-grants-1999_11
Patent number
US05981541

Reaction notes

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