Acetone → 6051-53-2

HRID 714190Notes

Reaction equation

HRID 714190 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH3:10][C:11]([CH3:13])=[O:12].[OH-].[Na+].Cl>C(O)C.O>[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[CH:10][C:11](=[O:12])[CH3:13]

Participants

7

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 6998SalicylaldehydeHCID 14798Sodium Hydroxide

Product 1

HCID 979566051-53-2Yield 26.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

2-Hydroxybenzaldehyde (1q, 0.90 ml, 8.4 mmol) and acetone (19, 1.24 ml, 16.8 mmol) were combined in ethanol (7 ml) and stirred for 15 min at room temperature. A solution of sodium hydroxide (0.5 g, 12.5 mmol) and water (2 ml) was added dropwise and the mixture stirred for 48 hr at room temperature. The mixture was neutralized with hydrochloric acid (1 N), extracted with ethyl acetate, washed with saturated sodium chloride, dried over magnesium sulfate, filtered and evaporated to afford a solid. The crude solid was recrystallized from tetrahydrofuran/hexane to give 0.36 g (26%) of a yellow solid: mp 136-137° C. [expected mp 139-140° C.]; 1H NMR: δ 2.42 (s, 3H), 6.92 (m, 2H), 7.03 (d, 1H, J=16.5 Hz), 7.24 (dt, 1H, J=7.0, 1.4 Hz), 7.45 (d, 1H, J=7.7 Hz), 7.88 (d, 1H, J=16.3 Hz), 8.00 (s, 1H); 13C NMR: δ 26.8, 116.6, 120.5, 127.5, 129.5, 131.9, 141.0, 156.1, 156.1, 201.3.

Workup

  1. stirringthe mixture stirred for 48 hr at room temperature
  2. extractionextracted with ethyl acetate
  3. washwashed with saturated sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customto afford a solid
  8. customThe crude solid was recrystallized from tetrahydrofuran/hexane

Sources & evidence

ORD record
ord-ae50754d1c344fbe87f7412e0e46c50e
Source dataset
uspto-grants-2015_11
Patent number
US09187397B2

Reaction notes

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