Lithium Hydroxide → 4-Tert-butyl-3-cyanobenzoic acid

HRID 2204171Notes

Reaction equation

HRID 2204171 reaction equation
[C:1]([C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11]C)=[O:10])=[CH:7][C:6]=1[C:15]#[N:16])([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-]>O1CCOCC1>[C:1]([C:5]1[CH:14]=[CH:13][C:8]([C:9]([OH:11])=[O:10])=[CH:7][C:6]=1[C:15]#[N:16])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 58551042Methyl 4-tert-butyl-3-cyano-benzoate

Product 1

HCID 585516854-Tert-butyl-3-cyanobenzoic acidYield 98%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of methyl 4-tert-butyl-3-cyano-benzoate (380 mg, 1.75 mmol), LiOH (3.5 mL of 2.0 M, 7.0 mmol) and 1,4-dioxane (3.5 mL) was heated at 60° C. for 2 h. The reaction mixture was made acidic and was washed with dichloromethane (2×8 mL). The organics were combined, dried over sodium sulfate and evaporated to dryness to give 4-tert-butyl-3-cyanobenzoic acid (348 mg, 98%). 1H NMR (400 MHz, CD3CN) δ 9.77 (s, 1H), 8.31 (d, J=1.8 Hz, 1H), 8.17 (dd, J=8.4, 1.9 Hz, 1H), 7.71 (d, J=8.4 Hz, 1H), 1.55 (s, 9H).

Workup

  1. washwas washed with dichloromethane (2×8 mL)
  2. dry with materialdried over sodium sulfate
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-5bcbd23b02144b19acaa57073f4d747d
Source dataset
uspto-grants-2016_06
Patent number
US09365588B2

Reaction notes

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