1,3-Propanediol → HCID 59792474, compound

HRID 31660Notes

Reaction equation

HRID 31660 reaction equation
[C:1]([O:9][CH2:10][C:11](=[O:14])[CH2:12][CH3:13])(=[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>C(OCC)C.C(OCC)(=O)C>[C:1]([O:9][CH2:10][C:11]1([CH2:12][CH3:13])[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

7

Reactant 4

HCID 104421,3-PropanediolHCID 31214Ethyl orthoformateHCID 521998p-Toluenesulfonic acid monohydrateHCID 157432722-Oxobutyl benzoate

Product 1

HCID 59792474HCID 59792474, compoundYield 66.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-oxobutyl benzoate (5 g, 26 mmol), 1,3-propanediol (5.94 g, 78 mmol), triethyl orthoformate (3.85 g, 26 mmol) and p-toluenesulfonic acid monohydrate (448 mg, 2.36 mmol) was stirred at room temperature for 3 hours and 30 minutes. To the reaction mixture, ethyl acetate and diethyl ether were added and the mixture was washed with water and a saturated saline solution. The organic layer was dried over sodium sulfate and filtrated. The filtrate was concentrated under reduced pressure. The residue was dissolved in heptane/ethyl acetate (12/1) and subjected to NH silica gel column chromatography (elution solvent: n-heptane/ethyl acetate=12/1) to obtain the title compound (4.33 g, 65.5%) as a colorless viscous oil.

Workup

  1. washthe mixture was washed with water
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltrated
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. dissolutionThe residue was dissolved in heptane/ethyl acetate (12/1)
  6. washsubjected to NH silica gel column chromatography (elution solvent: n-heptane/ethyl acetate=12/1)

Sources & evidence

ORD record
ord-522ab4777ab3407bb8ebfd6a32e8457c
Source dataset
uspto-grants-2008_09
Patent number
US07425634B2

Reaction notes

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