Hydrochloric Acid → HCID 60169542, compound

HRID 1855243Notes

Reaction equation

HRID 1855243 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[N:18][OH:19])[CH2:9][O:10][CH:11]([CH:16]=[CH2:17])[C:12]([F:15])([F:14])[F:13].C1(C=CC(O)=CC=1)O.Cl>>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]12[CH2:9][O:10][CH:11]([C:12]([F:15])([F:14])[F:13])[CH:16]1[CH2:17][O:19][NH:18]2

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 785HydroquinoneHCID 866683671-(2-Fluorophenyl)-2-(1,1,1-trifluorobut-3-en-2-yloxy)ethanone oxime

Product 1

HCID 60169542HCID 60169542, compound

Conditions

Temperature
128 °C

Procedure

To a solution of 1-(2-fluorophenyl)-2-(1,1,1-trifluorobut-3-en-2-yloxy)ethanone oxime 4 (1.085 kg, 3.328 mol) in xylenes (6.9 L) was added hydroquinone (86.2 g, 0.8 mol) at rt. The solution was heated to 128° C. (internal temperature) for 18 h. The solution was cooled to rt, and hexanes (7.0 L) was added, followed by 4.0 M aq. HCl (2.4 L). The reaction mixture was stirred for 1 h, and filtered. To the solid was added water (2.0 L), methyl tert-butyl ether (7.0 L) and 25% wt. aq. NaOH (0.4 L). The aq, layer was extracted once with methyl tert-butyl ether (7.0 L), the organics were combined, washed with 27% aq. NaCl (2.0 L) and concentrated under vacuum to a black oil 5 (512.0 g, 56%).

Workup

  1. temperatureThe solution was cooled to rt
  2. filtrationfiltered
  3. additionTo the solid was added water (2.0 L), methyl tert-butyl ether (7.0 L) and 25% wt. aq. NaOH (0.4 L)
  4. extractionThe aq, layer was extracted once with methyl tert-butyl ether (7.0 L)
  5. washwashed with 27% aq. NaCl (2.0 L)
  6. concentrationconcentrated under vacuum to a black oil 5 (512.0 g, 56%)

Sources & evidence

ORD record
ord-23829728c7854236a0b0df762359a01e
Source dataset
uspto-grants-2015_02
Patent number
US08962858B2

Reaction notes

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