Hydrochloric Acid → 3'-(Trifluoromethyl)acetophenone

HRID 1740541Notes

Reaction equation

[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)N.S(=O)(=O)(O)O.N([O-])=O.[Na+].[CH:21](=NO)[CH3:22].C(=O)(O)[O-:26].[Na+].Cl>>[CH3:22][C:21]([C:5]1[CH:7]=[CH:8][CH:9]=[C:3]([C:2]([F:11])([F:10])[F:1])[CH:4]=1)=[O:26]

Participants

Reactant 6

HCID 313Hydrochloric Acid

HCID 1118Sulfuric Acid

HCID 73753-(Trifluoromethyl)aniline

HCID 7863Aldoxime

HCID 516892Sodium Bicarbonate

HCID 23668193Sodium Nitrite

Product 1

HCID 676823'-(Trifluoromethyl)acetophenoneYield 70%

Procedure

A third example is described in Research Disclosure (1997), 402 (Oct) P706 (No. 40221), (CA 127:294925h). This reference teaches the multi-step reaction of 3-trifluoromethylaniline sequentially with a) aqueous sulfuric acid, b) aqueous sodium nitrite, c) aqueous acetaldoxime, d) cuprous sulfate and sodium bicarbonate and e) hydrochloric acid to form 3-trifluoromethylacetophenone in 70% yield. However, the overall volume efficiency of this process scheme is very low.

Sources & evidence

ORD record: ord-528ffe8cd6f24901856553a6267fec81
Source dataset: uspto-grants-1999_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05969188

Reaction notes

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