Formaldehyde → HCID 13389577, compound

HRID 1381369Notes

Reaction equation

HRID 1381369 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH:12]1[O:16][C:15](=[O:17])[CH:14]([C:18](O)=O)[CH:13]1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(=O)C.[Na+].C=O.C(NCC)C>C(O)(=O)C>[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH:12]1[O:16][C:15](=[O:17])[C:14](=[CH2:18])[CH:13]1[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 8021DiethylamineHCID 517045Sodium AcetateHCID 13389575HCID 13389575, compound

Product 1

HCID 13389577HCID 13389577, compoundYield 76.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

5-(3-Benzyloxypropyl)-2-oxo-4-phenyltetrahydro-3-furancarboxylic acid (1 g) 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. After cooling, the reaction mixture was poured into ice water and extracted with ether. The extract was washed with 5% sodium bicarbonate and water and dried over magnesium sulfate. The solvent was then distilled off to give 5-(3-benzyloxypropyl)-3-methylene-4-phenyltetrahydro-2-furanone (0.7 g) as a colorless oil.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ether
  3. washThe extract was washed with 5% sodium bicarbonate and water
  4. dry with materialdried over magnesium sulfate
  5. distillationThe solvent was then distilled off

Sources & evidence

ORD record
ord-4914b7a7d5dd4abeb74402169184a776
Source dataset
uspto-grants-1986_04
Patent number
US04585789

Reaction notes

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