Methanol → HCID 89581450, compound

HRID 1501084Notes

Reaction equation

HRID 1501084 reaction equation
O.[OH-].[Li+].[O:4]([CH:11]1[CH2:20][CH2:19][CH2:18][C:17]2[CH:16]=[C:15]([C:21]([O:23]C)=[O:22])[CH:14]=[CH:13][C:12]1=2)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.O1CCCC1.CO>O>[O:4]([CH:11]1[CH2:20][CH2:19][CH2:18][C:17]2[CH:16]=[C:15]([C:21]([OH:23])=[O:22])[CH:14]=[CH:13][C:12]1=2)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 89580639HCID 89580639, compound

Product 1

HCID 89581450HCID 89581450, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Lithium hydroxide hydrate (0.04 g, 1.0 mmol) was added to a solution of methyl 5-phenoxy-5,6,7,8-tetrahydronaphthalene-2-carboxylate (0.04 g, 0.14 mmol) in a mixed solution of tetrahydrofuran (6.0 mL), methanol (2 mL) and water (2 mL). The reaction mixture was stirred at room temperature for 1 hour. After the reaction, the solvent was removed in vacuo. Hydrochloric acid aqueous (3 mol/L) was added to make pH 3-5, and the mixture was extracted with dichloromethane. The combined organic phase was washed with water (20 mL×3), dried over anhydrous sodium sulfate. The mixture was filtered and the filtrate was concentrated to dryness to give pure product 5-phenoxy-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid as a white solid (0.032 g, 86%).

Workup

  1. customAfter the reaction
  2. customthe solvent was removed in vacuo
  3. additionHydrochloric acid aqueous (3 mol/L) was added
  4. extractionthe mixture was extracted with dichloromethane
  5. washThe combined organic phase was washed with water (20 mL×3)
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationThe mixture was filtered
  8. concentrationthe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-a51932c03ba442e8b01c9ddadbdcafa1
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

Loading…