Formaldehyde → Methyl 2-(4-chlorophenyl)-3-hydroxypropanoate

HRID 82270

Reaction equation

HRID 82270 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=1.[CH3:13][O-:14].[Na+].C=O>CS(C)=O.CCOC(C)=O>[CH3:1][O:2][C:3](=[O:12])[CH:4]([C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=1)[CH2:13][OH:14]

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 104196Methyl 4-chlorophenylacetateHCID 10942334Sodium Methoxide

Product 1

HCID 19914733Methyl 2-(4-chlorophenyl)-3-hydroxypropanoateYield 52%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of (4-Chloro-phenyl)-acetic acid methyl ester (2 g, 10.8 mmol) in DMSO (22 mL) was added sodium methoxide (29.2 mg, 0.54 mmol) at 0° C. Paraformaldehyde (342 mg, 11.4 mmol) was then added and the reaction mixture was stirred at room temperature for 4 hours. The reaction mixture was diluted with EtOAc (100 mL), washed with water (3×20 mL), brine (20 mL), dried (Na2SO4) and evaporated in vacuo. The crude material was purified by column chromatography on silica gel (gradient of hexane:EtOAc 100:0 to 84:16) to afford the title compound as a colourless gum in 52% yield, 1.2 g.

Workup

  1. washwashed with water (3×20 mL), brine (20 mL)
  2. dry with materialdried (Na2SO4)
  3. customevaporated in vacuo
  4. customThe crude material was purified by column chromatography on silica gel (gradient of hexane:EtOAc 100:0 to 84:16)

Sources & evidence

ORD record
ord-72356a2e90794135bb382226859174ee
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Linked notes

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