Acetone → HCID 51036371, compound

HRID 705467Notes

Reaction equation

HRID 705467 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[OH:11])[CH:6]=O.[CH3:14][C:15]([CH3:17])=[O:16].[OH2:18]>C(O)(=O)C.Cl>[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5](/[CH:6]=[CH:9]/[C:10](=[O:18])/[CH:3]=[CH:4]/[C:5]2[CH:6]=[CH:17][C:15]([OH:16])=[C:14]([C:2]([F:1])([F:12])[F:13])[CH:8]=2)[CH:8]=[CH:9][C:10]=1[OH:11]

Participants

6

Reactant 3

HCID 180AcetoneHCID 962WaterHCID 70215934-Hydroxy-3-(trifluoromethyl)benzaldehyde

Product 1

HCID 51036371HCID 51036371, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Conditions

Temperature
27.5 °C

Procedure

A mixture of 3-(trifluoromethyl)-4-hydroxybenzaldehyde (2.19 g, 12 mmol) in acetone (423 μL, 5.8 mmol) was dissolved in glacial acetic acid (9 mL), saturated with anhydrous HCl and heated to 25-30° C. for 2 h. The red solution was stirred for 36 h and treated with cold water. The reaction mixture turned into a dark green suspension and the resulting precipitate was filtered, washed with water and dried in vacuo to afford NW310.1 as a dark green solid (740 mg, 32%). mp: 233-234° C. 1H NMR (250 MHz, CD3OD) δ (ppm): 7.86 (d, 4J=1.6 Hz, 2H, HAr), 7.80 (d, 3J=8.8 Hz, 4J=1.9 Hz, 2H, HAr), 7.75 (d, 3J=16.1 Hz, 2H, Hvin), 7.15 (d, 3, J=15.9 Hz, 2H, Hvin), 7.02 (d, 3J=8.6 Hz, 2H, HAr). 13C NMR (75 MHz, CD3OD) δ (ppm): 191.6 (C), 159.9 (C), 144.3 (CH), 134.8 (CH), 129.3 (CH), 127.8 (C), 127.3 (C), 125.3 (CH), 118.8 (CH). MS (FAB) m/z: 403.2 (M+). Anal. calcd for C19H12F6O3. 1H2O: C, 54.17; H, 3.59. Found: C, 54.39; H, 3.31%.

Workup

  1. filtrationthe resulting precipitate was filtered
  2. washwashed with water
  3. customdried in vacuo

Sources & evidence

ORD record
ord-2824da846cc74a8688aea86276086c58
Source dataset
uspto-grants-2015_11
Patent number
US09174960B2

Reaction notes

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