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Water → (E)-3-(2,4-dibenzyloxyphenyl)prop-2-enoic acid

HRID 322848
Notes
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Reaction equation

HRID 322848 reaction equation
C([Li])CCC.[CH2:6]([C:8](CC)(P(O)(O)=O)[C:9]([OH:11])=[O:10])C.[CH2:18]([O:25][C:26]1[CH:33]=[C:32]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:31]=[CH:30][C:27]=1C=O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>O1CCCC1>[CH2:18]([O:25][C:26]1[CH:33]=[C:32]([O:34][CH2:35][C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH:31]=[CH:30][C:27]=1/[CH:6]=[CH:8]/[C:9]([OH:11])=[O:10])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 18090802,4-Bis(benzyloxy)benzaldehydeHCID 17786294Diethyl phosphonoacetic acidHCID 178418339Butyllithium

Product 1

HCID 10737234(E)-3-(2,4-dibenzyloxyphenyl)prop-2-enoic acidYield 36.7%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent
3×

Conditions

Temperature
-70 °C

Procedure

To a solution of 2.5 M n-butyl lithium (3.64 mL) in dry tetrahydrofuran (THF) (20 mL) that is cooled to −70° C. under nitrogen is added a solution of diethyl phosphonoacetic acid (0.89 g) in THF (5 mL). After 30 minutes a solution of 2,4-dibenzyloxybenzaldehyde (1.46 g) in THF (5 mL) is slowly added to the cooled solution so as to maintain the temperature. The resulting mixture is stirred at −70° C. for 3 hours and then at 25° C. for 18 hours. The resulting suspension is treated with water, the THF is removed in vacuo,the residue is extracted with ethyl acetate, the extract is dried and evaporated. The residual solid is recrystallized from isopropanol to yield (E)-3-(2,4-dibenzyloxyphenyl)prop-2-enoic acid as colourless crystals (0.6 g), m.p. 153-155° C. H NMR (DMSO) 5.15 (2H,s), 5.21(2H,s), 6.4(1H,d,J=16 Hz), 6.7(1H,d), 6.85(1H,s), 7.3-7.5(10H,m), 7.6(1H,d), 7.8(1H,d,J=16 Hz).

Workup

  1. temperatureto maintain the temperature
  2. waitat 25° C. for 18 hours
  3. customthe THF is removed in vacuo,the residue
  4. extractionis extracted with ethyl acetate
  5. customthe extract is dried
  6. customevaporated
  7. customThe residual solid is recrystallized from isopropanol

Sources & evidence

ORD record
ord-633593c12a7d4fa1bd1831ffcea2d9aa
Source dataset
uspto-grants-2001_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06211234B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes