Glycerol → HCID 20364909, compound

HRID 1678999Notes

Reaction equation

HRID 1678999 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[OH:10][CH2:11][CH:12]([CH2:14]O)[OH:13].S(=O)(=O)(O)O.O>C1C=CC=CC=1>[OH:13][CH:12]1[CH2:11][O:10][CH:5]([C:4]2[CH:7]=[CH:8][CH:9]=[C:2]([F:1])[CH:3]=2)[O:6][CH2:14]1

Participants

6

Reactant 4

HCID 753GlycerolHCID 962WaterHCID 1118Sulfuric AcidHCID 680093-Fluorobenzaldehyde

Product 1

HCID 20364909HCID 20364909, compoundYield 73.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 3-fluorobenzaldehyde (24.8 g, 0.2 mole), glycerol (18.4 g, 0.2 mole) and 40% sulfuric acid (2.0 ml) in benzene (200 ml) was heated with stirring under a Dean-Stark apparatus until water ceased to collect (approximately 2.5 hours). The mixture was cooled, neutralized with potassium carbonate and, after adding 200 ml of ether, washed with water (3 × 100 ml). The washed solution was dried over magnesium sulfate and concentrated under reduced pressure to give 29.0 g of colorless oil which was distilled under 0.025 mm using a short path distillation apparatus to give 18.9 g, nD24 1.5160, of 5-hydroxy-2-(3-fluorophenyl)-1,3-dioxane which distilled at a bath temperature of 86°-105° C.

Workup

  1. temperaturewas heated
  2. customto collect (approximately 2.5 hours)
  3. temperatureThe mixture was cooled
  4. additionafter adding 200 ml of ether
  5. washwashed with water (3 × 100 ml)
  6. dry with materialThe washed solution was dried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-585c9a5375ce43ef9bd607175daf1f56
Source dataset
uspto-grants-1978_03
Patent number
US04077982

Reaction notes

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