Water → HCID 21930377, compound

HRID 1178480Notes

Reaction equation

HRID 1178480 reaction equation
[OH:1][C:2]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].C(=O)([O-])[O-].[K+].[K+].I[CH2:18][CH2:19][CH3:20].O>CN(C=O)C>[OH:10][C:9]1[C:2]([O:1][CH2:18][CH2:19][CH3:20])=[C:3]([CH:6]=[CH:7][CH:8]=1)[CH:4]=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 905792,3-Dihydroxybenzaldehyde

Product 1

HCID 21930377HCID 21930377, compoundYield 42.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2,3-Dihydroxybenzaldehyde (1.16 g, 8.40 mmol), potassium carbonate (1.16 g, 8.40 mmol) and 1-iodopropane (0.82 mL, 1.43 g, 8.40 mmol) in dry DMF (10 mL) were stirred at ambient temperature for 20 h. The reaction mixture was poured into water and extracted with diethyl ether. The diethyl ether layer was washed with water (2×), then extracted with 1N sodium hydroxide solution (3×). The basic extracts were combined and acidified by addition of 3N hydrochloric acid, then extracted with diethyl ether. The ether layer was washed with 10% sodium hydrogen carbonate (3×), water (1×), brine (1×), and dried over MgSO4. After filtration, the solvent was removed in vacuo to yield 3-hydroxy-2-propoxybenzaldehyde (0.64 g, 42%) as a yellow solid.

Workup

  1. extractionextracted with diethyl ether
  2. washThe diethyl ether layer was washed with water (2×)
  3. extractionextracted with 1N sodium hydroxide solution (3×)
  4. additionacidified by addition of 3N hydrochloric acid
  5. extractionextracted with diethyl ether
  6. washThe ether layer was washed with 10% sodium hydrogen carbonate (3×), water (1×), brine (1×)
  7. dry with materialdried over MgSO4
  8. filtrationAfter filtration
  9. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-98fa3ea182e142e5ae06045d8a7dc684
Source dataset
uspto-grants-2007_10
Patent number
US07276528B2

Reaction notes

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