Methanol → (2,6-Diethylphenyl)methanol

HRID 409374Notes

Reaction equation

HRID 409374 reaction equation
C([O:4][CH2:5][C:6]1[C:11]([CH2:12][CH3:13])=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:14][CH3:15])(=O)C.CO.[OH-].[Na+]>O>[CH2:14]([C:7]1[CH:8]=[CH:9][CH:10]=[C:11]([CH2:12][CH3:13])[C:6]=1[CH2:5][OH:4])[CH3:15]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 667416382,6-Diethylbenzyl acetate

Product 1

HCID 13383922(2,6-Diethylphenyl)methanolYield 113.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2,6-diethylbenzyl acetate (2.11 g, 10.2 mmol), MeOH (20 mL), H2O (6 mL), and NaOH (1.99 g, 50 mmol, 5 eq) was stirred at RT overnight. After concentrating, the mixture was extracted with heptane (50 mL). The organic layer was dried (Na2SO4), filtered, and evaporated to give 1.90 g of title product. 1H NMR (300 MHz, CDCl3) δ 1.23 (t, 1H, OH), 1.24 (t, 6H), 1.37 (br s, 1H), 2.79 (q, 4H), 4.75 (d, 2H), 7.09 (d, 2H), 7.21 (dd, 1H). The following compound was prepared by making appropriate substitutions to the above procedure: (2,6-Dimethylphenyl)methanol. 1H NMR (300 MHz, CDCl3) δ 1.25 (t, 1H, OH), 2.41 (s, 6H), 4.72 (d, 2H), 7.0-7.15 (m, 3H).

Workup

  1. concentrationAfter concentrating
  2. extractionthe mixture was extracted with heptane (50 mL)
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-5860234a3ef64557b560ff5e5016b200
Source dataset
uspto-grants-2014_06
Patent number
US08759340B2

Reaction notes

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