Water → HCID 23373104, compound

HRID 1898999Notes

Reaction equation

HRID 1898999 reaction equation
[H-].[Na+].[CH3:3][C:4]1[C:11]([OH:12])=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=[O:7].[CH2:13](I)[CH2:14][CH3:15].O>CN(C=O)C>[CH3:3][C:4]1[C:11]([O:12][CH2:13][CH2:14][CH3:15])=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=[O:7]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 336431-IodopropaneHCID 5858763-Hydroxy-2-methylbenzaldehyde

Product 1

HCID 23373104HCID 23373104, compoundYield 35.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (1.15 g, 50% in oil) was added to a stirred solution of 2-methyl-3-hydroxybenzaldehyde (3.00 g) in dry DMF (30 ml). The mixture was stirred for 1 h at room temperature under nitrogen, then n-propyl iodide (4.49 g) was added portionwise over 20 min, followed by stirring for 1 h. The mixture was poured into water and extracted with diethyl ether, and the combined extracts dried (MgSO4) and evaporated to dryness. Purification by chromatography (SiO2 ; hexane/ethyl acetate) gave 2-methyl-3-n-propyloxybenzaldehyde (1.38 g).

Workup

  1. stirringby stirring for 1 h
  2. extractionextracted with diethyl ether
  3. dry with materialthe combined extracts dried (MgSO4)
  4. customevaporated to dryness
  5. customPurification by chromatography (SiO2 ; hexane/ethyl acetate)

Sources & evidence

ORD record
ord-2d80b65acb8d470c9e6cb4124987a15c
Source dataset
uspto-grants-1996_11
Patent number
US05571833

Reaction notes

Loading…