Water → (2R,6R)-2-(2'-phenylethyl)-6-methyl-1,3-dioxan-4-one

HRID 703698

Reaction equation

HRID 703698 reaction equation
[OH:1][C@H:2]([CH3:7])[CH2:3][C:4]([OH:6])=[O:5].[C:8]1([CH2:14][CH2:15][CH:16]=O)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH+]1C=CC=CC=1.O>ClCCl>[C:8]1([CH2:14][CH2:15][C@H:16]2[O:5][C:4](=[O:6])[CH2:3][C@@H:2]([CH3:7])[O:1]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7707BenzenepropanalHCID 921353-Hydroxybutanoic acid, (R)-HCID 22033616Pyridinium.p-toluenesulfonate

Product 1

HCID 13741776(2R,6R)-2-(2'-phenylethyl)-6-methyl-1,3-dioxan-4-oneYield 63.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (R)-3-hydroxybutanoic acid (7.8 g), 3-phenylpropionaldehyde (6.71 g) and pyridinium toluene-4-sulphonic acid (ca. 10 mmol %) in dichloromethane (300 ml) was stirred, under reflux, for 48 hours with removal of water. The reaction mixture was cooled to room temperature, washed three times with saturated sodium bicarbonate, dried (MgSO4) and evaporated under reduced pressure. The residue was crystallised from ether/pentane to give (2R,6R)-2-(2'-phenylethyl)-6-methyl-1,3-dioxan-4-one (7.0 g), m.p. 49.7°-50.9° C.; [α]DR.T. =15.2(c=1.05; CHCl3).

Workup

  1. washwashed three times with saturated sodium bicarbonate
  2. dry with materialdried (MgSO4)
  3. customevaporated under reduced pressure
  4. customThe residue was crystallised from ether/pentane

Sources & evidence

ORD record
ord-3bd0cb45f70b4fdf90c5a012c3b7f681
Source dataset
uspto-grants-1991_01
Patent number
US04983766

Linked notes

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