Acetone → HCID 51036372, compound

HRID 705468Notes

Reaction equation

HRID 705468 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][C:3]=1[O:10][C:11]([F:14])([F:13])[F:12].[CH3:15][C:16]([CH3:18])=[O:17].[OH2:19]>C(O)(=O)C.Cl>[OH:1][C:2]1[CH:9]=[CH:8][C:5](/[CH:6]=[CH:9]/[C:2](=[O:1])/[CH:3]=[CH:4]/[C:5]2[CH:8]=[CH:18][C:16]([OH:17])=[C:15]([O:19][C:11]([F:12])([F:13])[F:14])[CH:6]=2)=[CH:4][C:3]=1[O:10][C:11]([F:14])([F:13])[F:12]

Participants

6

Reactant 3

HCID 180AcetoneHCID 962WaterHCID 70180504-Hydroxy-3-(trifluoromethoxy)benzaldehyde

Product 1

HCID 51036372HCID 51036372, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Conditions

Temperature
27.5 °C

Procedure

A mixture of 4-hydroxy-3-(trifluoromethoxy)benzaldehyde (600 mg, 2.9 mmol) in acetone (107 μL, 1.5 mmol) was dissolved in glacial acetic acid (8 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 red suspension turned dark green. The resulting precipitate was filtered, washed with water and dried in vacuo to afford NW317 as a yellow-green solid (314 mg, 50%). mp: 103-105° C. 1H NMR (300 MHz, CD3OD) δ (ppm): 7.72 (d, 3J=15.9 Hz, 2H, Hvin), 7.62 (s, 2H, HAr), 7.58 (dd, 3J=8.5 Hz, 4J=2.0 Hz, 2H, HAr), 7.13 (d, 3J=15.9 Hz, 2H, Hvin), 7.03 (d, 3J=8.4 Hz, 2H, HAr). 13C NMR (75 MHz, CD3OD) δ (ppm): 191.2 (C), 153.8 (C), 143.8 (CH), 138.4 (C), 130.1 (CH), 128.4 (C), 125.0 (CH), 124.4 (CH), 120.5 (CH). MS (FAB) m/z: 435.2 (M+). Light-sensitive!

Workup

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

Sources & evidence

ORD record
ord-d07b6d1952df48e28b4ef137564ebc8f
Source dataset
uspto-grants-2015_11
Patent number
US09174960B2

Reaction notes

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