4-Hydroxybenzaldehyde → HCID 86645079, compound

HRID 1404649Notes

Reaction equation

HRID 1404649 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:10][O:9]2)[CH:5]=[CH:6][CH:7]=1.[OH:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=[O:17])=[CH:14][CH:13]=1.[OH-].[Na+]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([OH:9])[CH2:10][O:11][C:12]2[CH:19]=[CH:18][C:15]([CH:16]=[O:17])=[CH:14][CH:13]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 14798Sodium HydroxideHCID 1556132-(3-Chlorophenyl)oxirane

Product 1

HCID 86645079HCID 86645079, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
78 °C

Procedure

To a stirring solution of 2-(3-chlorophenyl)oxirane (6.20 g, 40.0 mmol) in toluene (65 mL) was added 4-hydroxybenzaldehyde (7.30 g, 60.0 mmol), 1M NaOH (65 mL) and PEG4000 (polyethylene glycol, 0.85 g) and the stirring mixture was heated at 78° C. for three hours. The reaction was allowed to cool to RT and then extracted with EtOAc (2×150 mL). The combined extracts were washed with brine, dried (Na2SO4), filtered and evaporated in vacuo. The resulting light brown oil was adsorbed onto silica gel and chromatographed eluting with 25-40% EtOAc/hexanes. There are 2 major spots. Fractions containing the higher Rf spot were combined and evaporated in vacuo to give 1.08 g (10%) of the desired product as a colorless oil. Fractions containing the lower Rf spot were combined and evaporated in vacuo to give 0.95 g (8%) of the regioisomer as a colorless oil, 44B. Some starting epoxide (2.85 g) was also recovered.

Workup

  1. temperatureto cool to RT
  2. extractionextracted with EtOAc (2×150 mL)
  3. washThe combined extracts were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customchromatographed
  8. washeluting with 25-40% EtOAc/hexanes
  9. additionFractions containing the higher Rf spot
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-40d547a89a0c476ca1e32eab8c572631
Source dataset
uspto-grants-2014_12
Patent number
US08912335B2

Reaction notes

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