Phosphorus oxide (P4O10) → 3-(4-Biphenylyl)-2-butenoic acid ethyl ester

HRID 1582688Notes

Reaction equation

HRID 1582688 reaction equation
O[C:2]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:12][CH:11]=1)([CH3:9])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>C1C=CC=CC=1>[C:13]1([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:14]=[CH:15][C:10]([C:2]([CH3:9])=[CH:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 14812Phosphorus oxide (P4O10)HCID 12455957Ethyl 3-hydroxy-3-([1,1'-biphenyl]-4yl)butanoate

Product 1

HCID 545016723-(4-Biphenylyl)-2-butenoic acid ethyl esterYield 106.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of ethyl 3-hydroxy-3-([1,1′-biphenyl]-4yl)-butanoate (2e, 11 g) in benzene (250 ml) was added phosphorus pentoxide (4 g) and refluxed for 3 h. The benzene layer was decanted and then concentrated. The crude product was purified by column chromatography on silica gel to furnish 11 g (57.3% yield) of ethyl 3-([1,1′-biphenyl]-4yl)-but-2-enoate (3e, formula 3, R=Ph) m.p. 76-78° C.

Workup

  1. temperaturerefluxed for 3 h
  2. customThe benzene layer was decanted
  3. concentrationconcentrated
  4. customThe crude product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-bc5bc0267e3a466c8ef97aeb2ea726e8
Source dataset
uspto-grants-2004_05
Patent number
US06737438B2

Reaction notes

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