4-Methyloxybenzyl chloride → HCID 71272208, compound

HRID 475067Notes

Reaction equation

HRID 475067 reaction equation
[O:1]=[C:2]1[CH2:5][CH:4]([C:6]([OH:8])=[O:7])[CH2:3]1.C([O-])(O)=O.[Na+].[CH3:14][O:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20]Cl)=[CH:18][CH:17]=1>C(Cl)Cl.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[O:1]=[C:2]1[CH2:5][CH:4]([C:6]([O:8][CH2:20][C:19]2[CH:22]=[CH:23][C:16]([O:15][CH3:14])=[CH:17][CH:18]=2)=[O:7])[CH2:3]1

Participants

7

Reactant 3

HCID 699934-Methyloxybenzyl chlorideHCID 516892Sodium BicarbonateHCID 49133583-Oxocyclobutane-1-carboxylic acid

Product 1

HCID 71272208HCID 71272208, compoundYield 37%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-oxocyclobutanecarboxylic acid (20.0 g, 175.3 mmol) in DCM (500 mL) was added satd. aq. NaHCO3 (293 mL), tetrabutyl ammonium bromide (75.3 g, 227.9 mmol) and 4-methoxybenzyl chloride (33.0 g, 210.4 mmol) and the mixture was stirred at RT overnight. After the reaction was completed, the mixture was diluted with water and twice extracted with DCM (250 mL). The organic layer was washed with water, dried (Na2SO4), filtered and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting with petroleum ether/EtOAc (8:1) to afford 15.2 g (37%) of 4-methoxybenzyl 3-oxocyclobutanecarboxylate as an off-white solid.

Workup

  1. extractiontwice extracted with DCM (250 mL)
  2. washThe organic layer was washed with water
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by SiO2 chromatography
  7. washeluting with petroleum ether/EtOAc (8:1)

Sources & evidence

ORD record
ord-71c6eb2bd5404d3bae77cd03da050724
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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