Diethyl Ether → 1-(2-Iodo-5-isopropoxy-4-methoxyphenyl)propanol

HRID 41920Notes

Reaction equation

HRID 41920 reaction equation
IC.[I:3][C:4]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([O:14][CH:15]([CH3:17])[CH3:16])=[CH:8][C:5]=1[CH:6]=[O:7].[NH4+].[Cl-].[CH3:20][CH2:21]OCC>>[I:3][C:4]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([O:14][CH:15]([CH3:17])[CH3:16])=[CH:8][C:5]=1[CH:6]([OH:7])[CH2:20][CH3:21]

Participants

5

Reactant 4

HCID 3283Diethyl Ether4×HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 111099932-Iodo-5-isopropoxy-4-methoxybenzaldehyde

Product 1

HCID 667609401-(2-Iodo-5-isopropoxy-4-methoxyphenyl)propanolYield 97%

Conditions

Temperature
0 °C

Procedure

A mixture of Mg turnings (585 mg, 24.1 g·atom) in dry Et2O (8.0 mL) was stirred at 0° C. under a nitrogen atmosphere then treated, dropwise, with a solution of iodomethane (2.25 mL, 28.1 mmol) in dry Et2O (7.0 mL). After 0.5 h a solution of aldehyde 5 (3.00 g, 9.38 mmol) in dry Et2O (10 mL) was added, dropwise, to the mixture that was then allowed to warm to 18° C. Stirring was continued at this temperature for 3 h then the reaction mixture was treated with NH4Cl (10 mL of a 20% w/v aqueous solution) followed by Et2O (20 mL). The separated organic phase was washed with H2O (1×10 mL) then dried (MgSO4), filtered and concentrated under reduced pressure to afford the title compound 7 (3.19 g, 97%) as an orange oil.

Workup

  1. additionthen treated
  2. temperatureto warm to 18° C
  3. stirringStirring
  4. washThe separated organic phase was washed with H2O (1×10 mL)
  5. dry with materialthen dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b4b4c796196d4c9fbabbe5a9f1564cc3
Source dataset
uspto-grants-2013_09
Patent number
US08536157B2

Reaction notes

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