Hydrochloric Acid → HCID 19622754, compound

HRID 1684049Notes

Reaction equation

HRID 1684049 reaction equation
[CH:1](=[O:13])[C:2]1[CH:12]=[C:9]([O:10][CH3:11])[C:7]([OH:8])=[C:4]([O:5][CH3:6])[CH:3]=1.I[CH2:15][CH2:16][OH:17].C(=O)([O-])[O-].[K+].[K+].Cl>O.CN(C=O)C>[CH3:11][O:10][C:9]1[CH:12]=[C:2]([CH:3]=[C:4]([O:5][CH3:6])[C:7]=1[O:8][CH2:15][CH2:16][OH:17])[CH:1]=[O:13]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8655SyringaldehydeHCID 11430Potassium CarbonateHCID 12225Iodoethanol

Product 1

HCID 19622754HCID 19622754, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Syringaldehyde (1.0 g,5.49 mmole), 2-iodo-1-ethanol (1.90 g,10.98 mmole) and potassium carbonate (1.90 g, 13.77 mmole) were added to 15 ml dry DMF and stirred for 24 hours at 80° C. under an argon atmosphere. The reaction mixture was added to 100 ml H2O and acidified with 10% HCl. The product was extracted into CHCl3, dried over MgSO4, and concentrated to an oil in vacuo. The remaining oil was purified by flash column chromatography using 1:1 hex/ethyl acetate as eluent (1.009 g, 81%). NMR: (CDCl3) 3.23,t,1H; 3.73,m,2H; 3.93,s,6H; 4.20,t,2H; 7.13,s,2H; 9.87,s,1H M.S. (CI): 227 (100%).

Workup

  1. extractionThe product was extracted into CHCl3
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated to an oil in vacuo
  4. customThe remaining oil was purified by flash column chromatography

Sources & evidence

ORD record
ord-32e43027d98541d1879626c0a96fe370
Source dataset
uspto-grants-1997_06
Patent number
US05639782

Reaction notes

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