Formaldehyde → HCID 23323871, compound

HRID 1381373Notes

Reaction equation

HRID 1381373 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH:12]([CH2:13][CH2:14][CH2:15][OH:16])[O:11][C:10](=[O:17])[CH:9]2[C:18](O)=O)=[CH:4][CH:3]=1.C([O-])(=O)C.[Na+].C=O.C(NCC)C>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH:12]([CH2:13][CH2:14][CH2:15][OH:16])[O:11][C:10](=[O:17])[C:9]2=[CH2:18])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 8021DiethylamineHCID 517045Sodium AcetateHCID 23323865HCID 23323865, compound

Product 1

HCID 23323871HCID 23323871, compoundYield 89.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

4-(4-Chlorophenyl)-5-(3-hydroxypropyl)-2-oxotetrahydro-3-furancarboxylic acid (640 mg) was dissolved in a solution (5 ml) prepared from sodium acetate (105 mg), acetic acid (4 ml), formalin (2.92 ml) and diethylamine (1 ml), and the solution was heated on a water bath (100° C.) for 30 minutes. The reaction mixture was poured into ice water (20 ml) and extracted with ether. The extract was washed with 5% aqueous sodium hydroxide and water and dried over magnesium sulfate. The solvent was then distilled off. The residue was subjected to silical gel column chromatography, elution being carried out with chloroform to give 4-(4-chlorophenyl)-5-(3-hydroxypropyl)-3-methylenetetrahydro-2-furanone (512 mg) as a colorless oil.

Workup

  1. extractionextracted with ether
  2. washThe extract was washed with 5% aqueous sodium hydroxide and water
  3. dry with materialdried over magnesium sulfate
  4. distillationThe solvent was then distilled off
  5. washThe residue was subjected to silical gel column chromatography, elution

Sources & evidence

ORD record
ord-ed77c697850a4f6c959835d1570fd92e
Source dataset
uspto-grants-1986_04
Patent number
US04585789

Reaction notes

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