1,3-Propanediol → (2-(Hydroxymethyl)-1,3-dioxan-2-yl)methyl benzoate

HRID 1645609Notes

Reaction equation

HRID 1645609 reaction equation
[C:1]([O:9][CH2:10][C:11](=[O:14])[CH2:12][OH:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:15](O)[CH2:16][CH2:17][OH:18].C(OCC)(OCC)OCC.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(OCC)(=O)C.O>[C:1]([O:9][CH2:10][C:11]1([CH2:12][OH:13])[O:18][CH2:17][CH2:16][CH2:15][O:14]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 104421,3-Propanediol2×HCID 31214Ethyl orthoformate2×HCID 521998p-Toluenesulfonic acid monohydrateHCID 142935913-Hydroxy-2-oxopropyl benzoate2×

Product 1

HCID 59792406(2-(Hydroxymethyl)-1,3-dioxan-2-yl)methyl benzoate

Reagents, catalysts & solvents 3

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of the mixture (0.5 g) containing 3-hydroxy-2-oxopropyl benzoate, 1,3-propanediol (0.932 ml, 12.9 mmol), triethyl orthoformate (0.428 ml, 2.58 mmol), and p-toluenesulfonic acid monohydrate (44.5 mg, 0.234 mmol) was stirred at room temperature for 4 days. Another mixture consisting of the mixture (4 g) containing 3-hydroxy-2-oxopropyl benzoate, 1,3-propanediol (7.46 ml, 103 mmol), triethyl orthoformate (3.42 ml, 20.6 mmol), and p-toluenesulfonic acid monohydrate (356 mg, 1.87 mmol) was stirred at 40° C. overnight. Two reaction mixtures were combined, water and ethyl acetate were added, and the organic layer was taken out. The organic layer was dried over magnesium sulfate and filtrated. The filtrate was concentrated under reduced pressure. The residue was dissolved in n-heptane/ethyl acetate (2/1) and toluene and subjected to silica gel column chromatography (elution solvent: n-heptane/ethyl acetate=3/2) to obtain the title compound (4.2 g).

Workup

  1. stirringwas stirred at 40° C. overnight
  2. customTwo reaction mixtures
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltrated
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. dissolutionThe residue was dissolved in n-heptane/ethyl acetate (2/1)
  7. washtoluene and subjected to silica gel column chromatography (elution solvent: n-heptane/ethyl acetate=3/2)

Sources & evidence

ORD record
ord-aaea2e0d90784afda0fba43e1f46913b
Source dataset
uspto-grants-2012_02
Patent number
US08124780B2

Reaction notes

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