Carbon Dioxide → HCID 14672052, compound

HRID 231614Notes

Reaction equation

HRID 231614 reaction equation
[CH:1]([C:5]1[CH:10]=[C:9](Br)[CH:8]=[C:7]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:6]=1[O:16][Si](C)(C)C)([CH2:3][CH3:4])[CH3:2].C(C1C=CC=C(C(C)(C)C)C=1O)(CC)C.BrBr.C([Li])CCC.Cl[Si](C)(C)C.[C:48](=[O:50])=[O:49].[OH-].[Na+]>BrCCBr.C1COCC1>[CH:1]([C:5]1[CH:10]=[C:9]([CH:8]=[C:7]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:6]=1[OH:16])[C:48]([OH:50])=[O:49])([CH2:3][CH3:4])[CH3:2]

Participants

10

Reactant 7

HCID 280Carbon DioxideHCID 6397ChlorotrimethylsilaneHCID 14798Sodium HydroxideHCID 24408BromineHCID 146720472-(1,1-Dimethylethyl)-6-(1-methylpropyl)phenolHCID 14672051HCID 14672051, compoundHCID 178418339Butyllithium

Product 1

HCID 14672052HCID 14672052, compound

Reagents, catalysts & solvents 2

HCID 78391,2-DibromoethaneCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of Mg (10 mmol), 2-s-butyl-4-bromo-6-t-butyl-1-trimethylsiloxy benzene [which is prepared from 2-s-butyl-6-t-butylphenol by sequential reactions with bromine (CH2Cl2), 0° C., 15 min) and n-butyllithium (THF, -78° C., 15 min)/chlorotrimethylsilane (-78° C. to -25° C., 18 hr)] and a few drops of 1,2-dibromoethane in 25 ml THF is heated at reflux for two hr and then is added to an excess of pulverized dry ice. The resulting slurry is stirred for 1 hr, then added to a 300 ml portion of 1N NaOH and stirred for 1 hr. The resulting mixture is washed with 3×100 ml portions of ether, and then is made acidic with excess 3N HCl. The product is extracted with 3×200 ml portions of ethyl acetate. The combined organic portions are dried (MgSO4), filtered, and concentrated in vacuo to give 3 -s-butyl-4-hydroxy-5-t-butylbenzoic acid, used in the next step without further purification.

Workup

  1. temperatureis heated
  2. temperatureat reflux for two hr
  3. stirringstirred for 1 hr
  4. washThe resulting mixture is washed with 3×100 ml portions of ether
  5. extractionThe product is extracted with 3×200 ml portions of ethyl acetate
  6. dry with materialThe combined organic portions are dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3873d3e9ceef450eb04988dffd9bba20
Source dataset
uspto-grants-1989_07
Patent number
US04847303

Reaction notes

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