Glycerol → 2-(3-Methylphenyl)-1,3-dioxan-5-ol

HRID 1678997Notes

Reaction equation

HRID 1678997 reaction equation
[CH3:1][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]([CH3:1])[CH:3]=2)[O:6][CH2:14]1

Participants

6

Reactant 4

HCID 753GlycerolHCID 962WaterHCID 1118Sulfuric AcidHCID 121053-Methylbenzaldehyde

Product 1

HCID 203649382-(3-Methylphenyl)-1,3-dioxan-5-olYield 64.6%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 3-methylbenzaldehyde (24.0 g, 0.2 mole), glycerol (18.4 g, 0.2 mole) and 40% sulfuric acid (2.0 ml) in 150 ml of benzene was heated under a Dean-Stark apparatus until no more water was collected (approximately 2.5 hours). The mixture was cooled, neutralized with potassium carbonate, diluted by the addition of 200 ml of ether and the ether solution washed with water (3 × 100 ml). The organic layer was dried over magnesium sulfate and concentrated to give a residue of 25.1 g of the desired 5-hydroxy-2-(3-methylphenyl)-1,3-dioxane nD25 1.5346.

Workup

  1. customwas collected (approximately 2.5 hours)
  2. temperatureThe mixture was cooled
  3. additiondiluted by the addition of 200 ml of ether
  4. washthe ether solution washed with water (3 × 100 ml)
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-48e93acf670d404cb14854e0374f593e
Source dataset
uspto-grants-1978_03
Patent number
US04077982

Reaction notes

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