Allyl Alcohol → 3-(4-(Hydroxymethyl)phenyl)propanal

HRID 1916532Notes

Reaction equation

HRID 1916532 reaction equation
[CH2:1]([OH:4])[CH:2]=[CH2:3].C([O-])(O)=O.[Na+].I[C:11]1[CH:18]=[CH:17][C:14]([CH2:15][OH:16])=[CH:13][CH:12]=1.CCOC(C)=O>O.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2].O>[OH:16][CH2:15][C:14]1[CH:17]=[CH:18][C:11]([CH2:3][CH2:2][CH:1]=[O:4])=[CH:12][CH:13]=1

Participants

9

Reactant 4

HCID 7858Allyl AlcoholHCID 8857Ethyl AcetateHCID 290124-Iodobenzyl alcoholHCID 516892Sodium Bicarbonate

Product 1

HCID 534252763-(4-(Hydroxymethyl)phenyl)propanal

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 16212273Tetrabutylammonium chloride hydrateCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

10.5 mL (152.8 mmol) allylalcohol, 18.8 g (62.2 mmol) Tetrabutylammonium chloride monohydrate, 12.8 g (152.8 mmol) NaHCO3 and 0.75 g (3.1 mmol) Pd(OAc)2 is added to a solution of 15.0 g (62.2 mmol) 4-iodobenzylalcohol in 100 mL DMF at RT under an N2 atmosphere and the reaction solution is heated to 60° C. for 3 h. The solvent is eliminated i.vac., the residue combined with 250 mL EtOAc and 80 mL water and suction filtered through a fibreglass filter. 80 mL NaCl solution are added to the filtrate, the phases are separated and the organic phase is dried over MgSO4. After the desiccant and solvent have been eliminated the residue is purified by column chromatography on silica gel (gradient: cyc/EtOAc 3:1 after cyc/EtOAc 1:1).

Workup

  1. filtrationfiltered through a fibreglass
  2. filtrationfilter
  3. addition80 mL NaCl solution are added to the filtrate
  4. customthe phases are separated
  5. dry with materialthe organic phase is dried over MgSO4
  6. customis purified by column chromatography on silica gel (gradient: cyc/EtOAc 3:1 after cyc/EtOAc 1:1)

Sources & evidence

ORD record
ord-041ad69736544f918c4e009bc3042ac1
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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