Lithium Hydroxide → HCID 67465958, compound
Reaction equation
[C:1]([C:3]([CH3:18])([O:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12]C)=[O:11])=[C:8]([O:16][CH3:17])[CH:7]=1)[CH3:4])#[N:2].[OH-].[Li+]>O1CCCC1.O>[C:1]([C:3]([CH3:18])([O:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([OH:12])=[O:11])=[C:8]([O:16][CH3:17])[CH:7]=1)[CH3:4])#[N:2]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 65 °C
Procedure
Methyl 4-(1-cyano-1-methyl-ethoxy)-2-methoxy-benzoate (340 mg, 1.36 mmol) was dissolved in tetrahydrofuran (5 mL) and water (5 mL). Lithium hydroxide (98 mg, 4.1 mmol) was added and reaction mixture was heated at 65° C. for 1 hour. The crude material was diluted with 10 mL of water and was extracted two times with ether. The ether extracts were discarded and the aqueous layer was made acidic with 4M HCl. The product was then extracted into ethyl acetate, dried over sodium sulfate, filtered, and evaporated to dryness to yield 4-(1-cyano-1-methyl-ethoxy)-2-methoxy-benzoic acid (78%) as a pale yellow solid. ESI-MS m/z calc 235.1, found 236.1 (M+1)+. Retention time: 1.29 minutes (3 min run).
Workup
- customreaction mixture
- extractionwas extracted two times with ether
- extractionThe product was then extracted into ethyl acetate
- dry with materialdried over sodium sulfate
- filtrationfiltered
- customevaporated to dryness
Sources & evidence
- ORD record
- ord-d7b783d1193146c49937d2dfadfc8eb0
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09365588B2
Reaction notes
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