Oxygen → 2-Methyl-3-buten-2-ol

HRID 2418958Notes

Reaction equation

HRID 2418958 reaction equation
[CH3:1][C:2](=[CH:4][CH3:5])[CH3:3].[O:6]=O.[BH4-].[Na+]>CO>[CH3:1][C:2](=[CH2:3])[CH:4]([OH:6])[CH3:5].[CH3:1][C:2]([OH:6])([CH:4]=[CH2:5])[CH3:3]

Participants

6

Reactant 3

HCID 977OxygenHCID 105532-Methyl-2-buteneHCID 4311764Sodium borohydride

Product 2

HCID 82572-Methyl-3-buten-2-olHCID 663293-Methyl-3-buten-2-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1.0 g (14.3 mmol) of 2-methyl-2-butene and 500 mg. of photosensitizing resin in 150 ml of methanol was irradiated as described above. The volume of oxygen uptake was measured. To the solution was added sodium borohydride, and after 5 min. the solution was extracted with ether (20 ml.) The ether solution was analyzed by gas chromatography to give 3-methylbut-3-ene-2-ol and 2-methylbut-3-ene-2-ol, in a 50:50 ratio, within experimental error. The ratio of these two products is the same as that observed when rose bengal or methylene blue are dissolved in methanol. Hence the same intermediate, singlet oxygen is involved in both processes. Radical oxidation leads to different products.

Workup

  1. extractionafter 5 min. the solution was extracted with ether (20 ml.) The ether solution

Sources & evidence

ORD record
ord-25130593ae3e4aafa738d96412f61950
Source dataset
uspto-grants-1978_08
Patent number
US04104204

Reaction notes

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