Acetic Acid → Delta-Valerolactone

HRID 1636980Notes

Reaction equation

HRID 1636980 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH:7]N1[C:12](=[O:13])[C:11]2=[CH:14]C=CC=[C:10]2C1=O.[C:19]([OH:22])(=[O:21])[CH3:20]>>[C:6]1(=[O:7])[O:1][CH2:2][CH2:3][CH2:4][CH2:5]1.[C:12]([OH:1])(=[O:13])[CH2:11][CH2:14][CH2:20][C:19]([OH:22])=[O:21].[C:12]1(=[O:13])[O:22][C:19](=[O:21])[CH2:20][CH2:10][CH2:11]1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 8894Tetrahydropyran4×HCID 10665N-Hydroxyphthalimide

Product 3

HCID 743Glutaric AcidYield 11%HCID 7940Glutaric anhydrideYield 9%HCID 10953Delta-ValerolactoneYield 28%

Conditions

Temperature
60 °C

Procedure

A mixture of 3 mmole of tetrahydropyran, 10 mole % of N-hydroxyphthalimide relative to tetrahydropyran, 0.5 mole % of acetylacetonatocobalt(II) Co(AA)2 relative to tetrahydropyran, and 5 ml of acetic acid was stirred for 15 hours at 60° C. under an oxygen atmosphere. The products in the reaction mixture were analyzed by gas chromarography, and, as a result, tetrahydropyran was converted into δ-valerolactone (yield 28%), glutaric acid (yield 11%) and glutaric anhydride (yield 9%) with a conversion of 67%.

Sources & evidence

ORD record
ord-3198ad5cce7e4f9fbead0f4d0814794d
Source dataset
uspto-grants-2000_03
Patent number
US06037477

Reaction notes

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