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

HRID 1373497Notes

Reaction equation

[CH:1](=[O:6])[CH2:2][CH2:3][CH2:4][CH3:5].[OH-].[K+].[C:9]1(=[O:14])[CH2:13][CH2:12][CH2:11][CH2:10]1.[OH-].[Na+].P(=O)(O)(O)O>C(=C1CCCC1=O)CCCC.O>[OH:6][CH:1]([CH:10]1[CH2:11][CH2:12][CH2:13][C:9]1=[O:14])[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

Conditions

Temperature: 15 °C

Procedure

Valeraldehyde having an acid value of 7.5 mg-KOH/g was used as the starting material. 224.6 g (2.67 mol) cyclopentanone, 100 g water and 9.7 g (0.116 mol) 48% NaOH were introduced into a 1-L four-necked flask, then the mixture was cooled to 15° C. under stirring, and 100 g (1.16 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 9.3 g (0.100 mol) 105% condensed phosphoric acid and separated into two layers at 40° C. The resulting organic layer was 343.7 g, and the aqueous layer was 99.9 g. The pH of the aqueous layer was 5.5. The organic layer was analyzed in the same manner as in Example 1. The result indicated that the reaction mixture contained 165.8 g (0.974 mol) 2-(1-hydroxy-n-pentyl)cyclopentanone (yield 84.9%), 4.58 g (0.030 mol) 2-pentylidene cyclopentanone and 10.1 g (0.060 mol; content 2.9%) cyclopentanone dimer, and the aqueous layer contained 6.7 g cyclopentanone. 116.7 g cyclopentanone and 16 g water could be recovered by distillation from the organic layer. The phosphoric acid contained in the aqueous layer, as determined by titration with NaOH for converting it into trisodium phosphate, was 0.251 mol.

Workup

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

Sources & evidence

ORD record: ord-5c3eb90298b547af92152b26e873048d
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07161041B2

Reaction notes

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