Lithium Hydroxide → HCID 67465958, compound

HRID 1908127Notes

Reaction equation

HRID 1908127 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

HCID 3939Lithium HydroxideHCID 67464161HCID 67464161, compound

Product 1

HCID 67465958HCID 67465958, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

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

  1. customreaction mixture
  2. extractionwas extracted two times with ether
  3. extractionThe product was then extracted into ethyl acetate
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-ac55b7bfb97f498ea1decff8a387d43e
Source dataset
uspto-grants-2013_12
Patent number
US08598164B2

Reaction notes

Loading…