Water → 4-(1-Allyl-1-hydroxymethyl-but-3-enyl)-benzoic acid methyl ester

HRID 658291Notes

Reaction equation

HRID 658291 reaction equation
[CH2:1]([C:4]([C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[CH:12][CH:11]=1)([CH2:8][OH:9])[CH2:5][CH:6]=[CH2:7])[CH:2]=[CH2:3].[C:19]([O-])([O-])=O.[K+].[K+].IC.O>CN(C=O)C>[CH3:19][O:15][C:14](=[O:16])[C:13]1[CH:17]=[CH:18][C:10]([C:4]([CH2:5][CH:6]=[CH2:7])([CH2:8][OH:9])[CH2:1][CH:2]=[CH2:3])=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 674858114-(1-Allyl-1-hydroxymethyl-but-3-enyl)-benzoic acid

Product 1

HCID 674860384-(1-Allyl-1-hydroxymethyl-but-3-enyl)-benzoic acid methyl esterYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-(1-allyl-1-hydroxymethyl-but-3-enyl)-benzoic acid (0.793 g, 3.22 mmol) in DMF (11.0 mL) is treated with K2CO3 (0.685 g, 4.96 mmol), and iodomethane (0.25 mL, 4.02 mmol), and stirred at room temperature overnight. The mixture is poured into water (25 mL) and extracted with EtOAc (3×25 mL). The combined extracts are washed with water, brine, dried over MgSO4, filtered, and concentrated. The residue is loaded onto silica gel and eluted with hexanes using a gradient of 0% to 75% EtOAc to give 0.774 g, (92%) of the title compound as a clear syrup. 1H NMR (CDCl3): δ 8.03-8.00 (m, 2H), 7.44-7.41 (m, 2H), 5.65-5.54 (m, 2H), 5.11-5.06 (m, 4H), 5.05-5.02 (m, 4H), 3.91 (s, 3H), 3.84 (d, 2H, J=6.2 Hz), 2.59-2.46 (m, 4H), 1.33 (t, 1H, J=6.2 Hz).

Workup

  1. extractionextracted with EtOAc (3×25 mL)
  2. washThe combined extracts are washed with water, brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. washeluted with hexanes using a gradient of 0% to 75% EtOAc

Sources & evidence

ORD record
ord-8a92e46003ce43ed90516b1969a6e985
Source dataset
uspto-grants-2011_12
Patent number
US08076374B2

Reaction notes

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