2,6-Di-tert-butylphenol → HCID 86745643, compound

HRID 1029538Notes

Reaction equation

HRID 1029538 reaction equation
[CH3:1][O:2][C:3]([C:5](Cl)=[O:6])=[O:4].[Al+3].[Cl-].[Cl-].[Cl-].[C:12]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([CH3:25])([CH3:24])[CH3:23])[C:17]=1[OH:26])([CH3:15])([CH3:14])[CH3:13]>ClCCl>[CH3:15][C:12]([C:16]1[CH:21]=[C:20]([C:5](=[O:6])[C:3]([O:2][CH3:1])=[O:4])[CH:19]=[C:18]([C:22]([CH3:25])([CH3:24])[CH3:23])[C:17]=1[OH:26])([CH3:13])[CH3:14]

Participants

5

Reactant 3

HCID 314052,6-Di-tert-butylphenolHCID 79846Methyl chloroglyoxylateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 86745643HCID 86745643, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

A dichloromethane (50 mL) solution of 13.6 g (106.5 mmol, 1.1 equiv.) of methyloxalylchloride is added over 15 minutes to a 0° C. stirred slurry of 14.2 g (106.5 mmol, 1.1 equiv.) of AlCl3 in 100 mL of dichloromethane under nitrogen atmosphere. The reaction is stirred at 0° C. for 5 minutes and treated with a dichloromethane (50 mL) solution of 20.0 g (96.9 mmol) of 2,6-di-t-butylphenol over 30 minutes. The reaction is stirred for 3 hours and poured onto 700 mL of ice water and the layers separated. The aqueous layer is extracted with diethyl ether (3×200 mL). The combined organic layers are washed with aqueous 1N HCl (200 mL), water (4×200 mL) and saturated aqueous NaCl, dried over Na2SO4 and concentrated in vacuo to give a yellow solid. Recrystallizing from n-pentane gives a first crop of 8.40 g (mp 85°-86° C.) and a second crop of 4.45 g (mp 82.5°-84° C.). The total yield is 12.85 g (28.33 g theor., 45%).

Workup

  1. stirringThe reaction is stirred for 3 hours
  2. customthe layers separated
  3. extractionThe aqueous layer is extracted with diethyl ether (3×200 mL)
  4. washThe combined organic layers are washed with aqueous 1N HCl (200 mL), water (4×200 mL) and saturated aqueous NaCl
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customto give a yellow solid
  8. customRecrystallizing from n-pentane
  9. customgives a first crop of 8.40 g (mp 85°-86° C.)

Sources & evidence

ORD record
ord-b31f7245ee4d4d31a506385e59329301
Source dataset
uspto-grants-1992_04
Patent number
US05102897

Reaction notes

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