3-Hydroxybenzaldehyde → HCID 57940803, compound

HRID 1437121Notes

Reaction equation

HRID 1437121 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].CC(C)([O-])C.[K+].Br[CH2:17][C:18]([O:20][CH:21]([CH3:23])[CH3:22])=[O:19]>CN(C=O)C>[CH:21]([O:20][C:18](=[O:19])[CH2:17][O:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:4]([CH:5]=[O:6])[CH:3]=1)([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 1013-HydroxybenzaldehydeHCID 121593Isopropyl bromoacetateHCID 23665647Potassium tert-butoxide

Product 1

HCID 57940803HCID 57940803, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-hydroxybenzaldehyde (6.75 g, 55.2 mmol) in DMF (55 mL) was stirred at room temperature under a nitrogen atmosphere as potassium tert-butoxide (6.2 g, 55.3 mmol) was added in portions. The resulting suspension was stirred an additional 15 minutes at room temperature before isopropyl bromoacetate (7.10 mL, 55.2 mmol) was added. The reaction was stirred at room temperature for 15 h and was then quenched with water (250 mL). The resulting aqueous solution was extracted with ethyl acetate, and the combined organic layers were washed several times with water, dried over MgSO4, filtered, and concentrated in vacuo. Purification via medium pressure liquid chromatography (0-10% hexane/ethyl acetate) afforded the title compound (5.2 g, 65%) as a clear oil. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.30 (d, 6H) 5.04-5.32 (m, 1H) 7.21-7.28 (m, 1H) 7.38 (s, 1H) 7.44-7.60 (m, 2H) 9.98 (s, 1H).

Workup

  1. additionwas added in portions
  2. additionwas added
  3. customwas then quenched with water (250 mL)
  4. extractionThe resulting aqueous solution was extracted with ethyl acetate
  5. washthe combined organic layers were washed several times with water
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification via medium pressure liquid chromatography (0-10% hexane/ethyl acetate)

Sources & evidence

ORD record
ord-5ae45ad6d0014a0b8eccc9fc13a73374
Source dataset
uspto-grants-2009_11
Patent number
US07622475B2

Reaction notes

Loading…