Glycerol → HCID 20364901, compound

HRID 1679003Notes

Reaction equation

HRID 1679003 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[OH:10][CH2:11][CH:12]([CH2:14]O)[OH:13].S(=O)(=O)(O)O>CCOCC>[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]1[O:10][CH2:11][CH:12]([OH:13])[CH2:14][O:5]1

Participants

5

Reactant 3

HCID 753GlycerolHCID 1118Sulfuric AcidHCID 67970o-Fluorobenzaldehyde

Product 1

HCID 20364901HCID 20364901, compoundYield 45.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2-fluorobenzaldehyde (24.8 g, 0.2, mole), glycerol (18.4 g, 0.2 mole) and 40% sulfuric acid (2 ml) was heated at 80°-100° C for 12 hours. The mixture cooled to room temperature and 100 ml of ether was added. The solution was washed with 2% potassium carbonate solution, dried over magnesium sulfate and concentrated under reduced pressure. The oil which remained (28.7 g) was distilled under 1 × 10-5 mm to give a product (18 g) which distilled at a pot temperature of 140°-145° C. This product was identified by infrared and elemental analysis as 5-hydroxy-2-(2-fluorophenyl)-1,3-dioxane.

Workup

  1. temperaturewas heated at 80°-100° C for 12 hours
  2. washThe solution was washed with 2% potassium carbonate solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. distillationwas distilled under 1 × 10-5 mm

Sources & evidence

ORD record
ord-56e39c9a3645431d8b1c9a19b10669a1
Source dataset
uspto-grants-1978_03
Patent number
US04077982

Reaction notes

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