Acetic Acid → HCID 131712701, compound

HRID 2286283Notes

Reaction equation

HRID 2286283 reaction equation
[N+:1]([CH2:4][CH:5]([OH:20])[CH:6]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[CH:8]=1)([O-])=O.[C:21]([OH:24])(=[O:23])[CH3:22].CCOCC>C(O)C.[Ni]>[NH2:1][CH2:4][CH:5]([OH:20])[CH:6]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[CH:8]=1.[C:21]([O-:24])(=[O:23])[CH3:22]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 3283Diethyl EtherHCID 20542459HCID 20542459, compound

Product 1

HCID 131712701HCID 131712701, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

Crude 3-nitro-1-phenyl-1-(m-chlorophenyl)propan-2-ol (43 g; 0.15 M) in ethanol (600 ml) containing acetic acid (9.3 ml:l equiv.) and RaNi (approx. 20 g.,) was hydrogenated at 250 p.s.i. H2 pressure for 4 hours. The mixture was filtered and evaporated to give a greenish oil. Trituration with ether (250 ml) gave the required product (34 g; 72%) as an off-white solid M.pt. 132°-137° C.

Workup

  1. filtrationThe mixture was filtered
  2. customevaporated
  3. customto give a greenish oil

Sources & evidence

ORD record
ord-6b1350efbecb4a7b9d13a5dd499651b8
Source dataset
uspto-grants-1982_04
Patent number
US04327228

Reaction notes

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