Sodium Methoxide → 2-(4-Octylphenyl)ethanol

HRID 1505019Notes

Reaction equation

HRID 1505019 reaction equation
C[O-].[Na+].C([O:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:12][CH:11]=1)(=O)C>CO>[CH2:16]([C:13]1[CH:12]=[CH:11][C:10]([CH2:9][CH2:8][OH:7])=[CH:15][CH:14]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 114827792-(4-octylphenyl)ethyl Acetate

Product 1

HCID 113108762-(4-Octylphenyl)ethanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Sodium methoxide (22.6 g) and methanol (450 mL) are charged into a 1 liter single neck round bottom flask equipped with a guard tube and stirred for few minutes to form a clear solution. A mixture of 4-octylphenethyl acetate (58 g) and methanol (50 mL) is added and the mass is stirred for 3 hours at room temperature. Methanol is evaporated and the residue is diluted with water (300 mL) and extracted with ethyl acetate (2×300 mL). The extracts are combined, dried with sodium sulphate and concentrated under vacuum to give crude as yellow color liquid. The crude is purified is by a silica gel column using 30% ethyl acetate/hexane as the eluent to yield the title compound. Yield: 56 g.

Workup

  1. customequipped with a guard tube
  2. customto form a clear solution
  3. additionis added
  4. stirringthe mass is stirred for 3 hours at room temperature
  5. customMethanol is evaporated
  6. additionthe residue is diluted with water (300 mL)
  7. extractionextracted with ethyl acetate (2×300 mL)
  8. dry with materialdried with sodium sulphate
  9. concentrationconcentrated under vacuum
  10. customto give crude as yellow color liquid
  11. customThe crude is purified

Sources & evidence

ORD record
ord-ef3d0304fa3e43008c812547cbcd050f
Source dataset
uspto-grants-2015_12
Patent number
US09216943B2

Reaction notes

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