Methanol → HCID 9946524, compound

HRID 347314Notes

Reaction equation

HRID 347314 reaction equation
[CH3:1][OH:2].[CH3:3][C:4]1([CH3:25])[CH2:13][CH2:12][C:11]([CH3:15])([CH3:14])[C:10]2[CH:9]=[C:8]([CH:16]3[C:21]4[CH:22]=[CH:23][O:24][C:20]=4[CH2:19][CH2:18][CH2:17]3)[CH:7]=[CH:6][C:5]1=2.[OH-:26].[Na+]>O>[CH3:3][C:4]1([CH3:25])[CH2:13][CH2:12][C:11]([CH3:14])([CH3:15])[C:10]2[CH:9]=[C:8]([CH:16]3[C:21]4[CH:22]=[C:23]([C:1]([OH:26])=[O:2])[O:24][C:20]=4[CH2:19][CH2:18][CH2:17]3)[CH:7]=[CH:6][C:5]1=2

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 21082642HCID 21082642, compound

Product 1

HCID 9946524HCID 9946524, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A methanol solution (20 mL) was mixed with 4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthalenyl)-4,5,6,7-tetrahydro-1-benzofuran]-2-carboxaldehyde (100 mg, 0.30 mmol, see example 1 part C for preparation), 5.0 N NaOH (10 mL) and Ag2O (138 mg, 0.59 mmol. The resulting black heterogeneous reaction mixture was allowed to stir at room temperature for a period of 17 hours. The reaction mixture was diluted with water and washed with ethyl ether. The ether washes were discarded and the aqueous mixture was made acidic (pH 3.0) using concentrated HCl. The resulting mixture was extracted with ether and dried over MgSO4. The solvent was evaporated in vacuo to yield 73 mg of pure solid.

Workup

  1. customThe resulting black heterogeneous reaction mixture
  2. washwashed with ethyl ether
  3. extractionThe resulting mixture was extracted with ether
  4. dry with materialdried over MgSO4
  5. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-9ce5a0a56c0642078fdc4abd2be5d976
Source dataset
uspto-grants-2007_02
Patent number
US07173134B2

Reaction notes

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