Formaldehyde → HCID 67458894, compound

HRID 625055Notes

Reaction equation

HRID 625055 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.C=O.[C:15](OCC)(=[O:17])C>CS(C)=O.C[O-].[Na+]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH2:15][OH:17])[C:9]([O:11][CH3:12])=[O:10])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 8857Ethyl AcetateHCID 2733233Methyl 2-(4-fluorophenyl)acetate

Product 1

HCID 67458894HCID 67458894, compoundYield 50.91%

Reagents, catalysts & solvents 2

HCID 10942334Sodium MethoxideCatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

Methyl 2-(4-fluorophenyl)acetate (5.0 g, 29.73 mmol), NaOMe (0.08031 g, 1.487 mmol) and paraformaldehyde (0.9374 g, 31.22 mmol) were dissolved/suspended in 200 mL of DMSO and allowed to stir overnight at ambient temperature. The reaction was quenched with the addition of 1000 mL of ice-cold water. The reaction was neutralized with the addition of HCl solution, and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with water twice, once with brine, separated, dried over MgSO4, filtered, and concentrated in vacuo to afford the crude product as a yellow oil. Column chromatography on silica gel eluting with 25:75 hexanes:ethyl acetate afforded methyl 2-(4-fluorophenyl)-3-hydroxypropanoate (3.0 g, 50.91% yield) as a colorless oil.

Workup

  1. customThe reaction was quenched with the addition of 1000 mL of ice-cold water
  2. additionThe reaction was neutralized with the addition of HCl solution
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washThe combined organic layers were washed with water twice
  5. customonce with brine, separated
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto afford the crude product as a yellow oil

Sources & evidence

ORD record
ord-70fc8d1840c146eaadbe362cbd72ea9b
Source dataset
uspto-grants-2016_04
Patent number
US09303040B2

Reaction notes

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