Water → HCID 22421095, compound

HRID 1441033Notes

Reaction equation

HRID 1441033 reaction equation
[OH:1][CH2:2][C:3]#[C:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][CH:6]=1.[C:13](OC(=O)C)(=[O:15])[CH3:14].C([O-])(=O)C.[Na+].O>C1C=CC=CC=1.CCCCCC.CCOCC>[C:13]([O:1][CH2:2][C:3]#[C:4][C:5]1[CH:6]=[CH:7][C:8]([CH:9]=[O:10])=[CH:11][CH:12]=1)(=[O:15])[CH3:14]

Participants

8

Reactant 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 41705854-(3-hydroxyprop-1-ynyl)benzaldehyde

Product 1

HCID 22421095HCID 22421095, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Procedure

To 4-(3-hydroxyprop-1-ynyl)benzaldehyde (500 mg.) in dry benzene (20 ml.) was added acetic anhydride (326 mg.) and anhydrous sodium acetate (112 mg.). The mixture was heated at reflux for 4 hours. After cooling, water (50 ml.) was added followed by ether (50 ml.). The organic layer was separated and washed with sodium carbonate solution (2×50 ml.), washed with water, dried over anhydrous magnesium sulphate and evaporated in vacuo. The product was isolated by column chromatography on silica eluting with ether:hexane; 1:1. Nuclear Magnetic Resonance (NMR) was as follows; 2.2, 3H, s; 5.0, 2H, s; 7.5, 4H, dd; 10.0, 1H, s.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 4 hours
  3. temperatureAfter cooling
  4. customThe organic layer was separated
  5. washwashed with sodium carbonate solution (2×50 ml.)
  6. washwashed with water
  7. dry with materialdried over anhydrous magnesium sulphate
  8. customevaporated in vacuo
  9. customThe product was isolated by column chromatography on silica eluting with ether

Sources & evidence

ORD record
ord-ea640d9a6ea748fb8422f9cb4c857d26
Source dataset
uspto-grants-1996_03
Patent number
US05502073

Reaction notes

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