Lithium Hydroxide → 3-(2-Cyanopropan-2-yl)benzoic acid

HRID 594029Notes

Reaction equation

HRID 594029 reaction equation
[C:1]([C:3]([C:6]1[CH:7]=[C:8]([CH:13]=[CH:14][CH:15]=1)[C:9]([O:11]C)=[O:10])([CH3:5])[CH3:4])#[N:2].[Li+].[OH-]>C1COCC1>[C:1]([C:3]([C:6]1[CH:7]=[C:8]([CH:13]=[CH:14][CH:15]=1)[C:9]([OH:11])=[O:10])([CH3:5])[CH3:4])#[N:2]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 57441035Methyl 3-(2-cyanopropan-2-yl)benzoate

Product 1

HCID 571495383-(2-Cyanopropan-2-yl)benzoic acidYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-(2-cyanopropan-2-yl)benzoate (1 equiv.) in THF (0.10 M) was added 1M LiOH (2.5 equiv.) and allowed to stir at RT for 18 hrs. LCMS analysis indicated the formation of the desired product (MH+—190, Rt—0.60 min). The volatiles were removed in vacuo, and the aqueous phase was acidified to ˜pH3 with 1M HCl. A white precipitate was formed, filtered and dried. Isolated 3-(2-cyanopropan-2-yl)benzoic acid in 63% yield. LCMS (m/z) (M+H)=190.1, Rt=0.60. 1H NMR (400 MHz, <cd3od>) δ ppm 1.76 (s, 6H) 7.54 (t, J=7.83 Hz, 1H) 7.74-7.80 (m, 1H) 8.00 (d, J=7.43 Hz, 1H) 8.16-8.21 (m, 1H).

Sources & evidence

ORD record
ord-3f8f19da86ea451bac3315e794c63cd3
Source dataset
uspto-grants-2016_01
Patent number
US09242969B2

Reaction notes

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