Mandelic Acid → HCID 18413067, compound

HRID 992663Notes

Reaction equation

[C:1]([OH:11])(=[O:10])[CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3].Br[CH:13]([CH3:17])[C:14](Br)=[O:15]>>[CH3:17][CH:13]1[C:14](=[O:15])[O:3][CH:2]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:1](=[O:11])[O:10]1

Participants

Reactant 2

HCID 1292Mandelic Acid

HCID 79047Propanoyl bromide, 2-bromo-

Product 1

HCID 18413067HCID 18413067, compoundYield 33%

Procedure

3-methyl-6-phenyl-2,5-dioxane-1,4-dione (9) was synthesized by using mandelic acid and 2-bromopropionyl bromide. Recrystallization from toluene gave white crystals. Mp 153-156° C. Yield: 33%. 1H NMR (CDCl3) δ7.43 (m, 5H), 5.92 (s, 1H) 5.17 (q, 1H), 1.63 (d, 3H). 13C NMR (CDCl3 δ166.90, 165.55, 131.24, 129.95, 128.92, 127.44, 77.74, 72.77, 16.42 MS (m/q) 207.4 (M+1).

Workup

customRecrystallization from toluene
customgave white crystals

Sources & evidence

ORD record: ord-b23ffc7949574c5b957b6e8d4f132457
Source dataset: uspto-grants-2002_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06469133B2

Reaction notes

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