Di-tert-butyl dicarbonate → Tert-butyl 2-[(tert-butoxycarbonyl)oxy]-6-methyl-3-(trifluoromethyl)benzoate

HRID 2076635Notes

Reaction equation

[C:1]([O:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])(OC(C)(C)C)=O.OC1[C:25]([C:26]([F:29])([F:28])[F:27])=[CH:24][CH:23]=[C:22]([CH3:30])[C:18]=1[C:19]([OH:21])=[O:20]>C(O)(C)(C)C.O1CCCC1>[C:12]([O:11][C:9]([O:8][C:1]1[C:25]([C:26]([F:27])([F:28])[F:29])=[CH:24][CH:23]=[C:22]([CH3:30])[C:18]=1[C:19]([O:21][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:20])=[O:10])([CH3:13])([CH3:14])[CH3:15]

Participants

Conditions

Temperature: 60 °C

Procedure

N,N-Dimethylaminopyridine (0.7 g, 5.7 mmol) and di-tert-butyl dicarbonate [(tBuOCO)2O] (16.7 g, 76.5 mmol) were added to a solution of 2-hydroxy-6-methyl-3-(trifluoromethyl)benzoic acid (4.21 g, 19.1 mmol) obtained in Example (28-3) in a mixture of tert-butyl alcohol-tetrahydrofuran (2:1, 60 ml), and the mixture was stirred at 60° C. for 3 hours. The reaction mixture was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=9/1) to give tert-butyl 2-[(tert-butoxycarbonyl)oxy]-6-methyl-3-(trifluoromethyl)benzoate (6.27 g, yield: 87%).

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customthe residue was purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=9/1)

Sources & evidence

ORD record: ord-76f0978fb0ee4b13915757cd3c5f9073
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07923573B2

Reaction notes

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