Hydrochloric Acid → GNF-Pf-1049

HRID 1614395Notes

Reaction equation

HRID 1614395 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[C:10]([CH3:15])([CH3:14])[CH2:9][CH2:8][C:7]2([CH3:17])[CH3:16])(=O)[CH3:2].[Cl-].[OH:19][NH3+:20].Cl>N1C=CC=CC=1>[N:20](=[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[C:10]([CH3:15])([CH3:14])[CH2:9][CH2:8][C:7]2([CH3:17])[CH3:16])[CH3:2])[OH:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21645Hydroxylamine HClHCID 27475621-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)ethan-1-one

Product 1

HCID 2747574GNF-Pf-1049Yield 100.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

15 g (65 millimoles) of 6-acetyl-1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalene and 6.5 g (91 millimoles) of hydroxylammonium chloride in 100 ml of pyridine were heated for 1 hour at 80° C. After cooling, the mixture was poured onto water and acidified with 2 N hydrochloric acid. The precipitated crystals were filtered off under suction, washed with water and dried. 16 g of 6-[1-hydroximinoethyl]-1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalene were obtained in this manner. 5 g (20 millimoles) thereof and 5 g (20 millimoles) of terephthalic monomethyl ester chloride were combined and were stirred for 6 hours at 120° C. After cooling, the solidified material was dissolved with about 60 ml of methanol. The supernatant methanol phase was decanted and the solid residue was recrystallized twice from chloroform/methanol. 2.5 g of the title compound of melting point 207°-208° C. were obtained in this manner.

Workup

  1. temperatureAfter cooling
  2. additionthe mixture was poured onto water
  3. filtrationThe precipitated crystals were filtered off under suction
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-03ff50fe72364215b32502a63c61fe2e
Source dataset
uspto-grants-1993_03
Patent number
US05196532

Reaction notes

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