tert-Butanol → HCID 90409143, compound

HRID 2275414Notes

Reaction equation

HRID 2275414 reaction equation
[OH:1][C:2]1[C:3]([CH3:15])=[C:4]([CH:9]=[CH:10][C:11]=1[CH:12]=CC)[C:5]([O:7][CH3:8])=[O:6].I([O-])(=O)(=O)=[O:17].[Na+].C(O)(C)(C)C>O1CCOCC1.O.[Os](=O)(=O)(=O)=O>[CH:12]([C:11]1[CH:10]=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[C:3]([CH3:15])[C:2]=1[OH:1])=[O:17]

Participants

6

Reactant 3

HCID 6386tert-ButanolHCID 23667635Sodium periodateHCID 90408745HCID 90408745, compound

Product 1

HCID 90409143HCID 90409143, compound

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

To a solution of methyl 3-hydroxy-2-methyl-4-(prop-1-en-1yl)benzoate (1.66 g, 8.05 mol) in dioxane/water (280 mL 2.5/1 ratio) was added sodium periodate (3.96 g, 18.51 mmol) and 2.5 wt % solution of osmium tetroxide in tert-butanol (3.3 ml, 2.66 mmol). The reaction mixture was stirred overnight at room temperature. LCMS showed a single peak with the expected product mass. After aqueous work up and extraction with EtOAc, the crude product was purified on ISCO system (40 g silica gel column, hexane/EtOAc gradient) to get 1.2 g (77% yield) of the aldehyde. 1H NMR (400 MHz, CDCl3) δ 11.39 (s, 1H), 9.93 (s, 1H), 7.45 (d, J=8.1 Hz, 1H), 7.38 (d, J=8.1 Hz, 1H), 3.93 (s, 3H), 2.44 (s, 3H).

Sources & evidence

ORD record
ord-8c9fe49e4a6f4a919bd57195996bcd62
Source dataset
uspto-grants-2015_09
Patent number
US09127024B2

Reaction notes

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