Methanol → HCID 12133075, compound

HRID 1765335Notes

Reaction equation

HRID 1765335 reaction equation
[C:1](Cl)(Cl)(Cl)Cl.[CH:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]([CH3:17])[CH3:16])[C:10]=1[OH:18])([CH3:8])[CH3:7].[CH3:19][OH:20].[OH-:21].[Na+]>[Cu].O>[CH3:19][O:20][C:1]([C:13]1[CH:14]=[C:9]([CH:6]([CH3:8])[CH3:7])[C:10]([OH:18])=[C:11]([CH:15]([CH3:17])[CH3:16])[CH:12]=1)=[O:21]

Participants

7

Reactant 4

HCID 887MethanolHCID 4943PropofolHCID 5943Carbon TetrachlorideHCID 14798Sodium Hydroxide

Product 1

HCID 12133075HCID 12133075, compound

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

Carbon tetrachloride (28 mL) was added dropwise to a mixture of 2,6-diisopropylphenol (37.5 mL), copper powder (2 g), methanol (150 mL), and 40% aqueous solution of sodium hydroxide (150 mL), at 40–50° C. The reaction temperature was warmed to about 60° C., and the resulting mixture was allowed to stir for 4 hours. The mixture was poured into water and extracted with toluene (3×). The combined organics were washed (brine), dried over sodium sulfate and concentrated. Chromatography with ethyl ether:hexanes as the eluent (gradient 5/95 to 8/92) provided material that precipitated as a white solid upon addition of hexane. The white solid was collected by filtration to provide the title compound (1.06 g); 1H-NMR(CDCl3) δ=1.29 (d, 12H, CH(CH3)2), 3.16 (m, 2H, CH (CH3)2), 3.87 (S, 3H, OCH3), 5.22 (S, 1H, OH), 7.78 (S, 2H, ArH).

Workup

  1. extractionextracted with toluene (3×)
  2. washThe combined organics were washed (brine)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customChromatography with ethyl ether:hexanes as the eluent (gradient 5/95 to 8/92) provided material
  6. customthat precipitated as a white solid upon addition of hexane
  7. filtrationThe white solid was collected by filtration

Sources & evidence

ORD record
ord-4687e56b63ff4e94b78305cfb65d898b
Source dataset
uspto-grants-2007_06
Patent number
US07226946B2

Reaction notes

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