Hydrochloric Acid → 5,6,7,8-Tetrahydro-3-methoxy5,5,8,8-tetramethyl-2-naphthaldoxime

HRID 2259804Notes

Reaction equation

HRID 2259804 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH:17]=O)=[CH:5][C:6]2[C:7]([CH3:16])([CH3:15])[CH2:8][CH2:9][C:10]([CH3:14])([CH3:13])[C:11]=2[CH:12]=1.[Cl-].[OH:20][NH3+:21].Cl>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[C:4]([CH:17]=[N:21][OH:20])=[CH:5][C:6]2[C:7]([CH3:16])([CH3:15])[CH2:8][CH2:9][C:10]([CH3:14])([CH3:13])[C:11]=2[CH:12]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21645Hydroxylamine HClHCID 147265222-Formyl-5,6,7,8-tetrahydro-3-methoxy-5,5,8,8tetramethylnaphthalene

Product 1

HCID 867451925,6,7,8-Tetrahydro-3-methoxy5,5,8,8-tetramethyl-2-naphthaldoximeYield 97.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5 g (20 millimoles) of 5,6,7,8-tetrahydro-3-methoxy-5,5,8,8-tetramethyl-2-naphthaldehyde and 2.1 g (30 millimoles) of hydroxylammonium chloride in 32.5 ml of dry pyridine were refluxed for 2 hours. The mixture was then allowed to cool, poured onto water and acidified with concentrated hydrochloric acid, and the precipitate which had separated out was filtered off under suction and dried to give 5.1 g of 5,6,7,8-tetrahydro-3-methoxy-5,5,8,8-tetramethyl-2-naphthaldoxime of melting point 182°-183° C.

Workup

  1. temperatureto cool
  2. additionpoured onto water
  3. customthe precipitate which had separated out
  4. filtrationwas filtered off under suction
  5. customdried

Sources & evidence

ORD record
ord-5b42ba65daf64a12b902989e1c33f7e6
Source dataset
uspto-grants-1995_12
Patent number
US05475017

Reaction notes

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