Sodium Hydroxide → 2,6-Di-sec-butylphenol

HRID 656794Notes

Reaction equation

HRID 656794 reaction equation
[CH:1]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH:11]([CH2:13][CH3:14])[CH3:12])[C:6]=1[O:15]C(=O)N)([CH2:3][CH3:4])[CH3:2].[OH-].[Na+]>O1CCOCC1>[CH:11]([C:7]1[CH:8]=[CH:9][CH:10]=[C:5]([CH:1]([CH2:3][CH3:4])[CH3:2])[C:6]=1[OH:15])([CH2:13][CH3:14])[CH3:12]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66725334Carbamic acid 2,6-di-sec-butylphenyl ester

Product 1

HCID 216852,6-Di-sec-butylphenolYield 100.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

R-(+)-1-Phenyl-ethyl)-carbamic acid (−)-2,6-di-sec-butylphenyl ester (1b) (4.1 g, 11.6 mmol) was dissolved in a 100 ml 1:1 mixture of dioxane: 1M NaOH aq. The reaction mixture was stirred at 70° C. for 15 min. Volatiles were removed at reduced pressure to a volume of ˜50-70 ml. The pH was adjusted to 3-4 with 1M HCl. The phenol was extracted with ether (3×50 ml), washed with 1 M HCl, brine and dried over anhydrous MgSO4. Evaporation yielded crude yellow oil (2.4 g, ˜100%). Vacuum distillation was performed (120-125° C./˜5 mm) (2.1 g, 89%). Optical rotation: α20D=−14.11° (c=2, pentane).

Workup

  1. customVolatiles were removed at reduced pressure to a volume of ˜50-70 ml
  2. extractionThe phenol was extracted with ether (3×50 ml)
  3. washwashed with 1 M HCl, brine
  4. dry with materialdried over anhydrous MgSO4
  5. customEvaporation

Sources & evidence

ORD record
ord-f1cd41664aa64e849f57788cd4e41764
Source dataset
uspto-grants-2011_12
Patent number
US08071818B2

Reaction notes

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