Water → HCID 10313776, compound

HRID 987883Notes

Reaction equation

HRID 987883 reaction equation
[I:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]([O:15]C)=[O:14])=[CH:8][CH:7]=1.[OH-].[Li+].O>CO>[I:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:12][C:13]([OH:15])=[O:14])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 10382060HCID 10382060, compound

Product 1

HCID 10313776HCID 10313776, compoundYield 85.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 4-(4-iodo-1-butyl)phenylacetate (21.28 g, 0.064 mol) was dissolved in methanol (160 mL). Lithium hydroxide (6.72 g, 0.16 mol) and water (10 mL) were added, and the reaction mixture was stirred for 18 hours at room temperature. The solvents were removed under reduced pressure, the residue was treated with ethyl acetate (600 mL), and the organic solution was washed with 1N HCl (3×300 mL), brine (3×300 mL), dried over MgSO4, and filtered. The filtrate was concentrated and dried in vacuo to give 17.5 g (85.9%) of 4-(4-iodo-1-butyl)phenylacetic acid as a yellow solid. 1H NMR (300 MHz, CD3OD) δ: 1.68-1.84 (m, 4H), 2.61 (t, 2H, J=7.35 Hz), 3.24 (t, 2H, J=6.75 Hz), 3.55 (s, 2H), 7.16 (ab quartet, 4H, J=8.26 Hz). FAB-MS m/z=319 (M+H); HRMS calcd for C12H16O2I (M+H) 319.0194, found 319.0208.

Workup

  1. customThe solvents were removed under reduced pressure
  2. additionthe residue was treated with ethyl acetate (600 mL)
  3. washthe organic solution was washed with 1N HCl (3×300 mL), brine (3×300 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. customdried in vacuo

Sources & evidence

ORD record
ord-3715e67f9583458c95f9568e4a2d3cca
Source dataset
uspto-grants-2003_10
Patent number
US06632921B1

Reaction notes

Loading…