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Carbon Dioxide → HCID 58236465, compound

HRID 1947174
Notes
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Reaction equation

HRID 1947174 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH:8]([CH3:10])[CH3:9])[C:5]([O:11][CH2:12][O:13][CH3:14])=[CH:4][C:3]=1[O:15][CH2:16][O:17][CH3:18].O1CCCC1.[Li+].CCC[CH2-].[C:29](=[O:31])=[O:30]>O.CCCCCC>[CH:8]([C:6]1[C:5]([O:11][CH2:12][O:13][CH3:14])=[CH:4][C:3]([O:15][CH2:16][O:17][CH3:18])=[C:2]([CH:7]=1)[C:29]([OH:31])=[O:30])([CH3:10])[CH3:9]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 8028TetrahydrofuranHCID 61028n-Butyl lithiumHCID 598298701-Bromo-5-isopropyl-2,4-bis-methoxymethoxy-benzene

Product 1

HCID 58236465HCID 58236465, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 8058HexaneSolvent

Conditions

Temperature
-60 °C

Procedure

1-bromo-5-isopropyl-2,4-bis-methoxymethoxy-benzene (IM2-a: 12.0 g, 37.8 mmol) and tetrahydrofuran (150 mL) were placed in a 300 mL three-neck flask and cooled to −60° C. To this mixture a hexane solution of N-butyllithium (24 mL, 1.59 M) was added slowly, and after adjusting the temperature of the solution to −40° C. the mixture was stirred for 1 hour. Dry ice powder was added to the reaction mixture and the reaction mixture was allowed to come to room temperature. After completing the reaction, the reaction mixture was mixed with distilled water and extracted with ethyl acetate. The extracted organic layer was dried over anhydrous sodium sulfate. After filtration and evaporation, the solid material obtained was purified by suspending in hexane to obtain the title compound (IM3-a: 6.6 g, 62%).

Workup

  1. customto −40° C.
  2. customto come to room temperature
  3. customthe reaction
  4. extractionextracted with ethyl acetate
  5. dry with materialThe extracted organic layer was dried over anhydrous sodium sulfate
  6. filtrationAfter filtration and evaporation
  7. customthe solid material obtained
  8. customwas purified

Sources & evidence

ORD record
ord-958e3b345d384a5cbb1cacd3eb9a872f
Source dataset
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08399464B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes