Sulfuric Acid → 2-Propyldecanoic acid

HRID 846553Notes

Reaction equation

C(C(CCCCCC)C[OH:5])C.[CH2:12]([CH:15]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:16][OH:17])[CH2:13][CH3:14].[Mn]([O-])(=O)(=O)=O.[K+].S(=O)(=O)(O)O>>[CH2:12]([CH:15]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:16]([OH:5])=[O:17])[CH2:13][CH3:14]

Participants

Reactant 4

HCID 1118Sulfuric Acid

HCID 893572-Ethyloctan-1-ol

HCID 516875Potassium Permanganate

HCID 144389072-Propyldecan-1-ol

Product 1

HCID 125447942-Propyldecanoic acid

Procedure

Instead of (-)-2-ethyl-1-octanol in Example 8, 5.07 g (25.3 mmol) of (-)-2-propyl-1-decanol was used and then oxidized with potassium permanganate under the same acidic state of sulfuric acid as in Example 6 to obtain 2-propyl decanoic acid. 2.19 g (10.2 mmol) of this compound was reacted with 1.75 g (14.7 mmol) of thionyl chloride under the same conditions as in Example 8 to obtain 2.39 g of a light brown liquid of (+)-2-propyldecanoic acid chloride having a specific rotation [α]25 of +1.63.

Sources & evidence

ORD record: ord-f9814c46e6f54244a70efd946a058101
Source dataset: uspto-grants-1992_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05137653

Reaction notes

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