Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → HCID 53720656, compound

HRID 850164Notes

Reaction equation

HRID 850164 reaction equation
[CH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[C:5]([O:12][CH3:13])[CH:4]=1)=O.C1(P(=[CH:33][C:34]([O:36][CH3:37])=[O:35])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[C:7]([C:6]1[CH:10]=[CH:11][C:3]([CH:1]=[CH:33][C:34]([O:36][CH3:37])=[O:35])=[CH:4][C:5]=1[O:12][CH3:13])([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 212546644-Formyl-2-methoxybenzoic acid

Product 1

HCID 53720656HCID 53720656, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 4-formyl-2-methoxybenzoic acid obtained above in tetrahydrofuran was added methyl (triphenylphosphoranylidene)acetate (3.3 g) at ambient temperature, and the mixture was stirred for 1 hour at the same temperature. The mixture was concentrated in vacuo, and ethyl acetate and saturated sodium bicarbonate solution were added thereto. The separated aqueous layer was adjusted to pH 4 with 1N hydrochloric acid and extracted with ethyl acetate. The extract was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was washed with hot diisopropyl ether to give methyl 4-carboxy-3-methoxycinnamate (1.2 g).

Workup

  1. concentrationThe mixture was concentrated in vacuo, and ethyl acetate and saturated sodium bicarbonate solution
  2. additionwere added
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. washThe residue was washed with hot diisopropyl ether

Sources & evidence

ORD record
ord-aba402ce256f448c9ed2f6a42043ada5
Source dataset
uspto-grants-2000_01
Patent number
US06015818

Reaction notes

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