Neopentyl glycol → Ethyl {[(5,5-dimethyl-2-phenyl-1,3-dioxan-2-yl)methyl]thio}acetate

HRID 254081Notes

Reaction equation

HRID 254081 reaction equation
[O:1]=[C:2]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:3][S:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7].[CH3:17][C:18]([CH3:23])([CH2:21]O)[CH2:19][OH:20]>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:17][C:18]1([CH3:23])[CH2:19][O:20][C:2]([CH2:3][S:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[O:1][CH2:21]1

Participants

5

Reactant 2

HCID 31344Neopentyl glycolHCID 13237653Ethyl [(2-oxo-2-phenylethyl)sulfanyl]acetate

Product 1

HCID 59351113Ethyl {[(5,5-dimethyl-2-phenyl-1,3-dioxan-2-yl)methyl]thio}acetateYield 76.2%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

Ethyl [(2-oxo-2-phenylethyl)thio]acetate (10.8 g, 45.3 mmol) was dissolved in toluene (250 ml). 2,2-Dimethyl-1,3-propanediol (37.6 g, 0.36 mol) and p-toluene sulfonic acid (cat., 500 mg) were added. The mixture was stirred at reflux in a Dean-Stark apparatus for two hours and at room temperature overnight. The mixture was concentrated under reduced pressure. The crude oil was purified by flash-chromatography (hexane:EtOAc-7:1) to give 11.2 g (70%) of the title compound as a colourless oil. 1H-NMR (CDCl3, 200 MHz): δ 0.6 (s, 3H), 1.2-1.3 (t, 3H), 1.4 (s, 3H), 3.0 (s, 2H), 3.2 (s, 2H), 3.5 (s, 4H), 4.1-4.2 (q, 2H), 7.3-7.6 (m, 5H).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customThe crude oil was purified by flash-chromatography (hexane:EtOAc-7:1)

Sources & evidence

ORD record
ord-09eacfb12e084f57a911472715499dba
Source dataset
uspto-grants-2011_01
Patent number
US07871998B2

Reaction notes

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