Water → HCID 12266563, compound

HRID 2373138

Reaction equation

HRID 2373138 reaction equation
[OH-].[Na+].[C:3]1([CH2:18]P(=O)(OCC)OCC)[CH:8]=[CH:7][C:6]([CH2:9]P(=O)(OCC)OCC)=[CH:5][CH:4]=1.[Br:27][C:28]1[CH:35]=[CH:34][C:31]([CH:32]=O)=[CH:30][CH:29]=1.O>C1C=CC=CC=1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[Br:27][C:28]1[CH:35]=[CH:34][C:31](/[CH:32]=[CH:18]/[C:3]2[CH:4]=[CH:5][C:6](/[CH:9]=[CH:32]/[C:31]3[CH:34]=[CH:35][C:28]([Br:27])=[CH:29][CH:30]=3)=[CH:7][CH:8]=2)=[CH:30][CH:29]=1

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 707414-BromobenzaldehydeHCID 78303Phosphonic acid, P,P'-(1,4-phenylenebis(methylene))bis-, P,P,P',P'-tetraethyl ester

Product 1

HCID 12266563HCID 12266563, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 241BenzeneSolvent

Procedure

50% aqueous sodium hydroxide (20 ml) was added to a solution of tetraethyl p-xylylenebisphosphonate (2.40 g, 6.35 mmol) (25) and 4-bromobenzaldehyde (2.41 g, 13.02 mmol) in 10 ml of benzene. Tetra-n-butylammonium iodide (148 mmg) was added and the mixture was refluxed under nitrogen for 1 hour. The reaction mixture was allowed to cool and diluted by the addition of water (25 ml). A yellow solid was collected and washed three times with water, methanol and ether. The product was purified by recrystallization from xylenes and was isolated in 61.9% (1.73 g) yield (Product is insoluble in standard solvents).

Workup

  1. temperaturethe mixture was refluxed under nitrogen for 1 hour
  2. temperatureto cool
  3. customA yellow solid was collected
  4. washwashed three times with water, methanol and ether
  5. customThe product was purified by recrystallization from xylenes
  6. customwas isolated in 61.9% (1.73 g)
  7. customyield (Product is insoluble in standard solvents)

Sources & evidence

ORD record
ord-c9179945d71441d98244d7e77c38dd4d
Source dataset
uspto-grants-2008_12
Patent number
US07459106B2

Linked notes

Loading…