Trifluoroacetic acid → HCID 18614298, compound

HRID 2268119Notes

Reaction equation

HRID 2268119 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([CH:24]=[CH:25][C:26]=1[O:27][CH3:28])[O:12][C:13]1[C:18]([CH3:19])=[CH:17][C:16]([N+:20]([O-:22])=[O:21])=[CH:15][C:14]=1[CH3:23])C1C=CC=CC=1.C(O)(C(F)(F)F)=O.C1(SC)C=CC=CC=1>>[OH:8][C:9]1[CH:10]=[C:11]([CH:24]=[CH:25][C:26]=1[O:27][CH3:28])[O:12][C:13]1[C:14]([CH3:23])=[CH:15][C:16]([N+:20]([O-:22])=[O:21])=[CH:17][C:18]=1[CH3:19]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7520ThioanisoleHCID 18614245HCID 18614245, compound

Product 1

HCID 18614298HCID 18614298, compoundYield 95.4%

Procedure

A solution of 4-(3-benzyloxy-4-methoxyphenoxy)-3,5-dimethylnitrobenzene (1.65 g), TFA (3.5 mL) and thioanisole (2.2 mL) were stirred for 4 h. The reaction was partitioned between ethyl acetate and water, the organic layer dried over sodium sulfate and concentrated in vacuo. Flash chromatography afforded 4-(3-hydroxy-4-methoxyphenoxy)-3,5-dimethylnitrobenzene (1.2 g) as a yellow oil.

Workup

  1. customThe reaction was partitioned between ethyl acetate and water
  2. dry with materialthe organic layer dried over sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e16fe9a1cf714d3880266ee602cd6636
Source dataset
uspto-grants-2001_12
Patent number
US06326398B1

Reaction notes

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