Salicylaldehyde → 140451-38-3

HRID 1479031Notes

Reaction equation

HRID 1479031 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].C([O-])([O-])=O.[K+].[K+].[CH3:16][O:17][C:18](=[O:22])[CH:19](Br)[CH3:20]>CN(C=O)C.CC(=O)OCC>[CH3:16][O:17][C:18](=[O:22])[CH:19]([O:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5])[CH3:20]

Participants

6

Reactant 3

HCID 6998SalicylaldehydeHCID 11430Potassium CarbonateHCID 95576Methyl 2-bromopropionate

Product 1

HCID 15732700140451-38-3Yield 91.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2-hydroxy-benzaldehyde (1 g; 8.19 mmol; 1 eq.), K2CO3 (3.4 g; 24.6 mmol; 3 eq.) and 2-bromo-propionic acid methyl ester (3.42 g; 20.5 mmol; 2.5 eq.) in DMF (50 mL) was stirred at 120° C. for 45 minutes then diluted with EA. The solution was washed with water (3×) then brine, dried over magnesium sulfate and concentrated in vacuo. Purification by column chromatography (15% to 33% EA in cyclohexane) afforded the title compound (1.56 g, 91%) as a colourless oil. HPLC (max plot) 96.3%; Rt 3.18 min.

Workup

  1. washThe solution was washed with water (3×)
  2. dry with materialbrine, dried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customPurification by column chromatography (15% to 33% EA in cyclohexane)

Sources & evidence

ORD record
ord-acbde90599bb491b9cdce1100cf7d670
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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