Benzene → HCID 13749687, compound

HRID 1965937Notes

Reaction equation

HRID 1965937 reaction equation
[Br:1]C1C=CC=CC=1C=O.[OH:10][CH2:11][C:12]([CH3:16])([CH2:14][OH:15])[CH3:13].[C:17]1([CH3:33])[CH:22]=[CH:21][C:20](S(OC2C=CC=CN=2)(=O)=O)=[CH:19][CH:18]=1.C1C=CC=CC=1>O>[Br:1][C:19]1[CH:18]=[C:17]([CH:33]2[O:15][CH2:14][C:12]([CH3:16])([CH3:13])[CH2:11][O:10]2)[CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 241BenzeneHCID 31344Neopentyl glycolHCID 811292-BromobenzaldehydeHCID 118586112-Pyridinol, 2-(4-methylbenzenesulfonate)

Product 1

HCID 13749687HCID 13749687, compoundYield 863%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution consisting of o-bromobenzaldehyde (150 mmol), neopentyl glycol (180 mmol), pyridyl p-tolylsulfonate (15 mmol) and benzene (800 ml) was refluxed and azeotropic dewatered for 6 hours. The reaction mixture was cooled and diluted with water. The aqueous phase was extracted with ethyl acetate. The combined organic phase was washed with saturated sodium chloride aqueous solution, dried (Na2SO4), filtrated, concentrated and column separated (eluant: n-hexane/ethyl acetate system) to give 35.1 g of a white solid ketal, yield 86%.

Workup

  1. temperaturewas refluxed
  2. temperatureThe reaction mixture was cooled
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. washThe combined organic phase was washed with saturated sodium chloride aqueous solution
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltrated
  7. concentrationconcentrated
  8. customcolumn separated (eluant: n-hexane/ethyl acetate system)

Sources & evidence

ORD record
ord-6d16285baf7f4b1b85e3402e8501ff5d
Source dataset
uspto-grants-2013_04
Patent number
US08420626B2

Reaction notes

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