Ethylene Glycol → HCID 22999142, compound

HRID 1166761Notes

Reaction equation

HRID 1166761 reaction equation
[OH:1][C:2]1[C:9]([O:10][CH3:11])=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[I:12].[CH2:13](O)[CH2:14][OH:15].Cl[Si](C)(C)C>ClCCl>[O:7]1[CH2:13][CH2:14][O:15][CH:6]1[C:5]1[CH:8]=[C:9]([O:10][CH3:11])[C:2]([OH:1])=[C:3]([I:12])[CH:4]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6397ChlorotrimethylsilaneHCID 79499Benzaldehyde, 4-hydroxy-3-iodo-5-methoxy-

Product 1

HCID 22999142HCID 22999142, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-hydroxy-3-iodo-5-methoxybenzaldehyde (20 g, 72 mmoles), ethylene glycol (8.0 mL, 144 mmoles), and chlorotrimethylsilane 36.5 mL, 0.29 moles) in dichloromethane (300 mL) was heated at reflux for 16 hours. The mixture was cooled to room temperature and washed with saturated sodium hydrogencarbonate (3×200 mL). The combined aqueous phases were; extracted with dichloromethane (3×150 mL). The combined organic extracts were washed with saturated sodium chloride (200 mL), dried over MgSO4 and evaporated in vacuo to afford 22.1 g (95%) of 4-[1,3]dioxolan-2-yl-2-iodo-6-methoxy-phenol. M.p. 120-121° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 hours
  3. washwashed with saturated sodium hydrogencarbonate (3×200 mL)
  4. extractionextracted with dichloromethane (3×150 mL)
  5. washThe combined organic extracts were washed with saturated sodium chloride (200 mL)
  6. dry with materialdried over MgSO4
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-2618d2ae4f49491096d2e7370de9f1b4
Source dataset
uspto-grants-2003_09
Patent number
US06613942B1

Reaction notes

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