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

HRID 1591120Notes

Reaction equation

HRID 1591120 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-15929f5ef3734c72a477bcdae3ef00a4
Source dataset
uspto-grants-1993_04
Patent number
US05206242

Reaction notes

Loading…