Methanol → HCID 22452626, compound

HRID 2185879Notes

Reaction equation

HRID 2185879 reaction equation
[I:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:5]=[C:4]([C:12]([O:14]C)=[O:13])[C:3]=1[O:16][CH3:17].[OH-].[Na+].CO>C1COCC1.O>[I:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:5]=[C:4]([C:12]([OH:14])=[O:13])[C:3]=1[O:16][CH3:17]

Participants

6

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 22452654HCID 22452654, compound

Product 1

HCID 22452626HCID 22452626, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 4-iodo-3-methoxy-5,6,7,8-tetrahydro-2-naphthalenecarboxylate (3.0 g, 8.67 mmol) in THF (12 mL) and H2O (4 mL) was added 10N NaOH (9 mL). Methanol was added dropwise until the cloudy solution became clear. After stirring overnight at room temperature, the THF was removed in vacuo. The aqueous solution was acidified to pH 2 with 1N HCl and resulting white precipitate was extracted with DCM (3×25 mL). The combined organic extracts were dried (Na2SO4), filtered and concentrated in vacuo to afford a light brown solid (2.8 g, 100%). 1H NMR (CDCl3) δ 7.83 (s, 1H), 3.92 (s, 3H), 2.77 (m, 4H), 1.78 (m, 4H). MS m/z 331 (M−H).

Workup

  1. customthe THF was removed in vacuo
  2. customresulting white precipitate
  3. extractionwas extracted with DCM (3×25 mL)
  4. dry with materialThe combined organic extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d1c3666996f04e009bd175d69052c9ae
Source dataset
uspto-grants-2002_06
Patent number
US06403601B1

Reaction notes

Loading…