Carbon Dioxide → 2-Phenylisobutyric acid

HRID 495109

Reaction equation

HRID 495109 reaction equation
[CH3:1][C:2]1([CH3:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=O)[CH2:3]1.[C:13]1([C:19]([CH3:24])([CH3:23])[C:20]([OH:22])=[O:21])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[CH2:25](Cl)[C:26]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)(C)[CH3:27].[Mg].C(=O)=O>>[C:13]1([C:19]([CH3:24])([CH3:23])[C:20]([OH:22])=[O:21])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[CH3:25][C:26]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([CH2:4][CH2:3][C:2]([CH3:1])([C:10]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:12])[CH3:27]

Participants

7

Reactant 5

HCID 280Carbon DioxideHCID 132222-Phenylisobutyric acid2×HCID 68191Neophyl chlorideHCID 3046283,3-Dimethyl-1-indanoneHCID 5462224Magnesium

Product 2

HCID 132222-Phenylisobutyric acidHCID 3167052,5-Dimethyl-2,5-diphenylhexane

Procedure

A convenient synthesis into 3,3-dimethyl indan-1-one is via the acid catalysed cyclisation of phenylisobutyric acid. The phenylisobutyric acid may be prepared by reaction of neophylchloride with magnesium followed by carbon dioxide under known conditions. Typically, one obtains phenylisobutyric acid in admixture with an unwanted coupling product 2,5-dimethyl-2,5-diphenyl hexane.

Sources & evidence

ORD record
ord-e9d2482638e5442e8234f0af31d5e552
Source dataset
uspto-grants-2009_05
Patent number
US07538243B2

Linked notes

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