Phosphoric Acid → Cyclopentanone, 2-(1-hydroxypentyl)-

HRID 1373496Notes

Reaction equation

[C:1]1(=[O:6])[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].P(=O)(O)(O)O.P([O-])([O-])([O-])=O.[Na+].[Na+].[Na+].[CH:22](=[O:27])[CH2:23][CH2:24][CH2:25][CH3:26]>C(=C1CCCC1=O)CCCC>[OH:27][CH:22]([CH:2]1[CH2:3][CH2:4][CH2:5][C:1]1=[O:6])[CH2:23][CH2:24][CH2:25][CH3:26]

Participants

Conditions

Temperature: 15 °C

Procedure

The aqueous layer and the distilled fraction of (b) were introduced into a 500-mL four-necked flask and then 48.2 g cyclopentanone (1.34 mol including a re-used cyclopentanone) and 1.96 g (0.0236 mol) 48% NaOH, including NaOH for converting phosphoric acid contained in the aqueous layer to trisodium phosphate were added thereto. The mixture was cooled to 15° C. under stirring, and 50.0 g (0.58 mol) valeraldehyde was added dropwise at the same temperature over 5 hours. Thereafter, the mixture was stirred at the same temperature for 2 hours. After the reaction was finished, the mixture was neutralized with 1.89 g (0.0203 mol) 105% condensed phosphoric acid and separated into two phases at 40° C. The pH of the aqueous layer was 5.5. The resulting organic layer was 170.7 g, and the aqueous layer was 4.72 g. The organic layer was analyzed in the same manner as in Example 1. The result indicated that the reaction mixture contained 82.4 g (0.484 mol) 2-(1-hydroxy-n-pentyl)cyclopentanone (yield 83.5%) and 2.25 g (0.015 mol) 2-pentylidene cyclopentanone.

Workup

additionwere added
stirringThereafter, the mixture was stirred at the same temperature for 2 hours
customseparated into two phases at 40° C

Sources & evidence

ORD record: ord-c3f49d2bbeeb4729bbe7286ec7b79832
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07161041B2

Reaction notes

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