3-Hydroxybenzaldehyde → HCID 242135, compound

HRID 714168Notes

Reaction equation

HRID 714168 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.[CH3:10][C:11]([CH3:13])=[O:12].[OH-:14].[Na+].Cl>C(O)C.O>[OH:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:7][C:8](=[O:14])[CH:9]=[CH:2][C:3]2[CH:4]=[CH:5][CH:13]=[C:11]([OH:12])[CH:10]=2)[CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 1013-HydroxybenzaldehydeHCID 180AcetoneHCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide

Product 1

HCID 242135HCID 242135, compoundYield 19%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

3-Hydroxybenzaldehyde (1p, 2.07 g, 17.0) and acetone (19, 0.62 ml, 8.4 mmol) were combined in ethanol (15 ml) and stirred for 15 min at room temperature. A solution of sodium hydroxide (1.00 g, 25.0 mmol) and water (4 ml) was added and the solution stirred for 48 hr at room temperature. The resulting 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 ethyl acetate to give 0.42 g (19%) of a brown solid: mp 190-195° C. [expected mp 198-200° C.]; 1H NMR: (DMSO) δ 6.83 (d, 2H, J=7.0 Hz), 7.22 (m, 8H), 7.68 (d, 2H, J=16.1 Hz), 9.63 (s, 2H); 13C NMR: (DMSO) δ 114.7, 117.5, 119.4, 125.4, 129.7, 135.8, 142.7, 157.5, 168.2.

Workup

  1. stirringthe solution 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 ethyl acetate

Sources & evidence

ORD record
ord-02233957f3574becb22b99963d86290a
Source dataset
uspto-grants-2015_11
Patent number
US09187397B2

Reaction notes

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