Methyl Benzoate → HCID 25257820, compound

HRID 1972108Notes

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]CO.C(OC(C)C)(C)C>>[C:1]([O:9][CH2:10][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 199606-Amino-1-hexanol

Product 1

HCID 25257820HCID 25257820, compoundYield 82%

Procedure

In an argon atmosphere, a mixture of methyl benzoate (3.0 mmol), 6-aminohexan-1-ol (3.6 mmol), Zn4(OCOCF3)6O (1.25 mol % in terms of the mole number of zinc atoms; in the following Examples, the amount will be similarly expressed in terms of the mole number of zinc atoms) and diisopropyl ether (5.0 ml) was heated to reflux for 18 hours, and as a result, 6-aminohexyl benzoate having an acylated hydroxyl group was obtained at a yield of 82% (the yield is based on the carboxylic acid ester. The same applies in the following). The yield of 6-benzoylaminohexyl benzoate in which an amino group and a hydroxyl group were both acylated, was 18%.

Workup

temperaturewas heated
temperatureto reflux for 18 hours

Sources & evidence

ORD record: ord-f2b154ea90cb485392678e16912e3347
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431709B2

Reaction notes

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