alpha-pentylfuran-2-methanol → 4-Hydroxy-5-pentylcyclopent-2-en-1-one

HRID 2413376Notes

Reaction equation

HRID 2413376 reaction equation
[CH2:1]([CH:6](O)[C:7]1[O:11][CH:10]=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH3:5].C(C1C(=O)CC([OH:23])C=1)CCCC>O>[CH2:1]([CH:6]1[CH:7]([OH:11])[CH:8]=[CH:9][C:10]1=[O:23])[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

4

Reactant 2

HCID 85710alpha-pentylfuran-2-methanolHCID 13158020HCID 13158020, compound

Product 1

HCID 131761314-Hydroxy-5-pentylcyclopent-2-en-1-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

In the same flask as used in Example 1, there were charged α-n-pentylfurfuryl alcohol (I-3) (33.6 g) and water (1680 g), and the mixture was stirred at 100° C. while adjusting to a pH of 4.6-5.0. The reaction mixture was treated in the same manner as in Example 1 to give a mixture (29.2 g) of 2-n-pentyl-3-hydroxy-4-cyclopentenone (II-3) and 2-n-pentyl-4-hydroxy-2-cyclopentenone (III-3). Yield, 87%.

Workup

  1. additionThe reaction mixture was treated in the same manner as in Example 1

Sources & evidence

ORD record
ord-84878518dbe14a3998a0735d571f092a
Source dataset
uspto-grants-1985_01
Patent number
US04496767

Reaction notes

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