Benzyloxalate → Benzyl hexanoate

HRID 326378Notes

Reaction equation

[CH2:1]([Mg]Cl)[CH2:2][CH2:3][CH3:4].[CH2:7]([O:14][C:15](=[O:19])[C:16]([O-])=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>>[C:15]([O:14][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(=[O:19])[CH2:16][CH2:1][CH2:2][CH2:3][CH3:4]

Participants

Reactant 2

HCID 19738602Benzyloxalate

HCID 178418265HCID 178418265, compound

Product 1

HCID 23367Benzyl hexanoate

Procedure

Alternatively, the compound of Example 3 was prepared by the Grignard reaction of n-butylmagnesium chloride with excess benzyloxalate to obtain desired product in 27% yield. 1H NMR (CDCl3, TMS) δ0.91 (t,3H), 1.35 (m,2H), 1.6 (m,2H), 2.85 (t,2H), 5.29 (s,2H), 7.4 (m,5H). Rf value is identical to Example 3.

Sources & evidence

ORD record: ord-679e9086e93d45efa03dcd99410a35b6
Source dataset: uspto-grants-1993_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05268374

Reaction notes

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