Hydrochloric Acid → [3-(2-Hydroxy-1-methylethyl)-4-nitrophenyl]phenylmethanone

HRID 2357145Notes

Reaction equation

HRID 2357145 reaction equation
[OH:1][CH2:2][CH:3]([C:5]1[CH:6]=[C:7]([C:14]2([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)OCCC[O:15]2)[CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[CH3:4].Cl>C(O)C.O>[C:14]([C:7]1[CH:8]=[CH:9][C:10]([N+:11]([O-:13])=[O:12])=[C:5]([CH:3]([CH3:4])[CH2:2][OH:1])[CH:6]=1)(=[O:15])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59386295HCID 59386295, compound

Product 1

HCID 59386296[3-(2-Hydroxy-1-methylethyl)-4-nitrophenyl]phenylmethanoneYield 91%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of 2-(3-(2-hydroxy-1-methylethyl)-4-nitrophenyl)-2-phenyl-1,3-dioxane (18) (23.6 g; approx. 69 mmol) in ethanol (350 mL) was added water (70 mL) under vigorous stirring. Concentrated hydrochloric acid (about 12 N aqueous solution, 35 mL) was then added drop wise. The reaction mixture was stirred at ambient temperature for 4 hours, diluted with water and extracted with ethyl acetate. The organic phase was successively washed with an aqueous, saturated solution of NaHCO3 and with water. The organic phase was then concentrated in vacuo and seeded with crystals of the product 4f to provide a yellow solid. Finally, the powdered solid was washed with hexane and air dried to yield 17.83 g (62.5 mmol, 91%) of a yellow powder. 1H NMR (250 MHz, DMSO-d6) δ 7.91-7.52 (m, 8H, arom.), 4.75 (br. s., 1H, OH), 3.53 (d, 2H, α-CH2), 3.23 (sextet, 1H, β-CH), 1.24 (d, 3H, γ-CH3).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was successively washed with an aqueous, saturated solution of NaHCO3
  3. concentrationThe organic phase was then concentrated in vacuo
  4. customto provide a yellow solid
  5. washFinally, the powdered solid was washed with hexane and air
  6. customdried

Sources & evidence

ORD record
ord-0adb48d2fe844b3ebedf6f2d406fc6f8
Source dataset
uspto-grants-2010_07
Patent number
US07759513B2

Reaction notes

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