4-Nitrophenethyl alcohol → 2-(4-Nitrophenyl)ethyl 3,5-bis-(1,1-dimethylethyl)-4-hydroxybenzoate

HRID 1356423Notes

Reaction equation

[C:1]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:13]=1[OH:14])[C:8]([OH:10])=[O:9])([CH3:4])([CH3:3])[CH3:2].[N+:19]([C:22]1[CH:27]=[CH:26][C:25]([CH2:28][CH2:29]O)=[CH:24][CH:23]=1)([O-:21])=[O:20].C1(N=C=NC2CCCCC2)CCCCC1>C1COCC1>[CH3:2][C:1]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:13]=1[OH:14])[C:8]([O:10][CH2:29][CH2:28][C:25]1[CH:24]=[CH:23][C:22]([N+:19]([O-:21])=[O:20])=[CH:27][CH:26]=1)=[O:9])([CH3:4])[CH3:3]

Participants

Conditions

Temperature: 20 °C

Procedure

In a 250 ml flask containing 80 ml of THF, under an argon atmosphere, 2.45 g (9.8 mmoles) of 3,5-di-tert-butyl-4-hydroxybenzoic acid, 1.8 g (10.8 mmoles) of 4-nitrobenzene-ethanol and 2.2 g (10.8 mmoles) of dicyclohexylcarbodiimide are introduced successively, under agitation. The reaction medium is agitated for 15 hours at 20° C. and the precipitate which appears is filtered out. The filtrate is washed with 2×30 ml of a saturated NaCl solution, the organic phase is dried over magnesium sulphate, filtered and concentrated under vacuum. The residue is then crystallized using di-isopropyl ether. The solid is recovered by filtration and 2.4 g (62%) of white crystals are obtained after drying. Melting point: 123.5-124.5° C.

Workup

filtrationthe precipitate which appears is filtered out
washThe filtrate is washed with 2×30 ml of a saturated NaCl solution
dry with materialthe organic phase is dried over magnesium sulphate
filtrationfiltered
concentrationconcentrated under vacuum
customThe residue is then crystallized
filtrationThe solid is recovered by filtration and 2.4 g (62%) of white crystals
customare obtained
customafter drying

Sources & evidence

ORD record: ord-a19d9293356a47728ef03a382c05a13b
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06586454B2

Reaction notes

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