3-Hydroxy-4-methylbenzaldehyde → HCID 68714672, compound

HRID 2266416Notes

Reaction equation

HRID 2266416 reaction equation
[Br-].[CH2:2]([PH3+])[CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].CC(C)([O-])C.[K+].[OH:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][C:23]=1[CH3:24])[CH:19]=O>O1CCCC1.COC(C)(C)C>[CH:19](/[C:18]1[CH:21]=[CH:22][C:23]([CH3:24])=[C:16]([OH:15])[CH:17]=1)=[CH:2]/[CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

6

Reactant 3

HCID 5851823-Hydroxy-4-methylbenzaldehydeHCID 22161009HCID 22161009, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 68714672HCID 68714672, compoundYield 88.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

Under an atmosphere of Argon, to a solution of n-hexylphosphonium bromide (1.07 g) in tetrahydrofuran (10 mL) was added potassium t-butoxide (336 mg) at room temperature and the solution was stirred for 30 minutes. After cooling in ice bath, 3-hydroxy-4-methylbenzaldehyde (136 mg) was added to the reaction solution, which was stirred at room temperature for 1.5 hours. The reaction solution was diluted with t-butyl methyl ether. The solution was washed with dilute hydrochloric acid, water and brine, dried over anhydrous sodium sulfate and concentrated. The obtained residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:4) to give the title compound (180 mg) having the following physical data.

Workup

  1. temperatureAfter cooling in ice bath
  2. stirringwas stirred at room temperature for 1.5 hours
  3. washThe solution was washed with dilute hydrochloric acid, water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe obtained residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:4)

Sources & evidence

ORD record
ord-23ca5c06538a48a2ba8344d32965c41a
Source dataset
uspto-grants-2010_12
Patent number
US07858650B2

Reaction notes

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