Methyl Benzoate → 8-Aminooctyl benzoate

HRID 1972109Notes

Reaction equation

[C:1]([O:9][CH3:10])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]CO.C(OC(C)C)(C)C>>[C:1]([O:9][CH2:10][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][NH2:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 3

HCID 7150Methyl Benzoate

HCID 7914Diisopropyl Ether

HCID 159198328-Amino-1-octanol

Product 1

HCID 248275708-Aminooctyl benzoateYield 90%

Procedure

In an argon atmosphere, a mixture of methyl benzoate (3.0 mmol), 8-aminooctan-1-ol (3.6 mmol), Zn4(OCOCF3)6O (1.25 mol % in terms of mole number) and diisopropyl ether (5.0 ml) was heated to reflux for 20 hours, and as a result, 8-aminooctyl benzoate was obtained at a yield of 90%. The yield of 8-benzoylaminooctyl benzoate was 7%.

Workup

temperaturewas heated
temperatureto reflux for 20 hours

Sources & evidence

ORD record: ord-b2e89456cb7c4dc193f22164bc6d6734
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431709B2

Reaction notes

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