Hydrochloric Acid → 2-Naphthol, 1-ethyl-

HRID 1400308

Reaction equation

HRID 1400308 reaction equation
O.Cl.[OH:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]=1[C:14](=O)[CH3:15]>[Zn].Cl[Hg]Cl.C1(C)C=CC=CC=1>[CH2:14]([C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:12]=[CH:13][C:4]=1[OH:3])[CH3:15]

Participants

7

Reactant 3

HCID 313Hydrochloric Acid2×HCID 962WaterHCID 684551-(2-Hydroxy-1-naphthyl)ethan-1-one

Product 1

HCID 30149752-Naphthol, 1-ethyl-Yield 84.3%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 24085Mercuric ChlorideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A single neck round-bottom flask was charged with 2.3 g of zinc, 0.23 g of HgCl2 and 4 mL of water. Then 37% HCl (0.1 mL) was added and the mixture stirred for 5 minutes. After this, 3 mL of toluene and 3.4 mL of 37% HCl were added and finally 1 g (5.37 mmol) of 1-(2-hydroxynaphthalen-1-yl)ethanone was added portion wise. The resulting mixture was heated at 110° C. for 18 h. The phases were separated and the organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to afford 780 mg (84% yield) of 1-ethylnaphthalen-2-ol as brown solid.

Workup

  1. customThe phases were separated
  2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2c3e26fb70f34b4fba43c97b6d55b38f
Source dataset
uspto-grants-2014_12
Patent number
US08906946B2

Linked notes

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