Oxygen → 2-Methyl-3-buten-2-ol

HRID 436242Notes

Reaction equation

HRID 436242 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-158feeb19b74470f87fa40e23747c754
Source dataset
uspto-grants-1977_02
Patent number
US04008136

Reaction notes

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