1-Butanol → 4-(5,5-Dimethyl-2-phenyl-1,3-dioxan-2-yl)-2-nitrobenzenamine

HRID 437793Notes

Reaction equation

HRID 437793 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:9])=[CH:4][C:3]=1[N+:16]([O-:18])=[O:17].[CH3:19][C:20]([CH3:25])([CH2:23]O)[CH2:21][OH:22].CC1C=CC(S(O)(=O)=O)=CC=1.C(O)CCC>O.CC1C=CC=CC=1>[CH3:19][C:20]1([CH3:25])[CH2:21][O:22][C:8]([C:5]2[CH:6]=[CH:7][C:2]([NH2:1])=[C:3]([N+:16]([O-:18])=[O:17])[CH:4]=2)([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[O:9][CH2:23]1

Participants

7

Reactant 4

HCID 2631-ButanolHCID 6101p-Toluenesulfonic acidHCID 31344Neopentyl glycolHCID 5969704-Amino-3-nitrobenzophenone

Product 1

HCID 214270964-(5,5-Dimethyl-2-phenyl-1,3-dioxan-2-yl)-2-nitrobenzenamineYield 55%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A mixture of 31.5 parts of (4-amino-3-nitrophenyl)phenylmethanone, 21 parts of 2,2-dimethyl-1,3-propanediol, 2 parts of 4-methylbenzenesulfonic acid, 40 parts of butanol and 450 parts of methylbenzene is stirred and refluxed for 16 hours with water-separator. The reaction mixture is cooled and washed with ammonium hydroxide. The organic phase is dried, filtered and evaporated. The residue is crystallized from 2,2'-oxybispropane, yielding 27.5 parts (55%) of 4-(5,5-dimethyl-2-phenyl-1,3-dioxan-2-yl)-2-nitrobenzenamine; mp. 139.8° C.

Workup

  1. temperatureThe reaction mixture is cooled
  2. washwashed with ammonium hydroxide
  3. customThe organic phase is dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue is crystallized from 2,2'-oxybispropane

Sources & evidence

ORD record
ord-c54708484dbc44dbad4de6294514ee63
Source dataset
uspto-grants-1977_06
Patent number
US04032536

Reaction notes

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