2-Ethenylphenol → HCID 58884383, compound

HRID 1765956Notes

Reaction equation

HRID 1765956 reaction equation
Cl[C:2]([O-:4])=[O:3].[CH:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[OH:13])=[CH2:6].[CH:14](N(C(C)C)CC)([CH3:16])[CH3:15].[CH:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1O)=[CH2:24].Cl[C:33]([O-])=O.C1CCCCC1.ClCCl>C1COCC1>[C:2](=[O:3])([O:4][C:28]1[CH:29]=[CH:30][C:25]([CH:23]=[CH2:24])=[CH:26][CH:27]=1)[O:13][C:8]1[C:9]([CH:14]([CH3:16])[CH3:15])=[CH:10][CH:11]=[CH:12][C:7]=1[CH:5]([CH3:33])[CH3:6]

Participants

6

Reactant 4

HCID 1354422-EthenylphenolHCID 21226386CarbonochloridateHCID 21916607Dichloromethane cyclohexaneHCID 131726486HCID 131726486, compound

Product 1

HCID 58884383HCID 58884383, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The reaction is based on that described by Whitcombe et al (J Am Chem Soc 117, 7105–7111 (1995)); the molar ratios were choroformate:vinylphenol: diisopropylethylamine 1:1.2. The vinylphenol was dissolved in dry THF and the base added; the flask was kept in an ice bath an the chlorformate added dropwise; the flask was allowed to get to room temperature and the reaction was monitored (TLC 60–40 cyclohexane-dichloromethane)), the solvent was removed and the raw mixture was dissolved in CH2Cl2. After extraction with water the organic layer was taken down to dryness and the monomer was separated by purification on a silica column using a stepwise gradient of CH2Cl2-hexane (from 5% CH2Cl2 to 80%). The analysis showed purity >98%. The overall reaction scheme for preparation of them monomer is illustrated in Reaction Scheme I.

Workup

  1. additionthe base added
  2. customthe flask was kept in an ice bath
  3. customto get to room temperature
  4. customwas removed
  5. dissolutionthe raw mixture was dissolved in CH2Cl2
  6. extractionAfter extraction with water the organic layer
  7. customthe monomer was separated by purification on a silica column
  8. customThe overall reaction scheme
  9. customfor preparation of them monomer
  10. customis illustrated in Reaction Scheme I

Sources & evidence

ORD record
ord-8333149159a34a1c9f630e14f198549d
Source dataset
uspto-grants-2007_06
Patent number
US07229836B2

Reaction notes

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