4-Methyloxybenzyl chloride → HCID 22035839, compound

HRID 1245559Notes

Reaction equation

HRID 1245559 reaction equation
[CH3:1][C:2]([CH3:8])([CH2:6][OH:7])[C:3]([OH:5])=[O:4].[CH3:9][O:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15]Cl)=[CH:13][CH:12]=1>COCCOC>[CH3:1][C:2]([CH3:8])([CH2:6][OH:7])[C:3]([O:5][CH2:15][C:14]1[CH:17]=[CH:18][C:11]([O:10][CH3:9])=[CH:12][CH:13]=1)=[O:4]

Participants

4

Reactant 2

HCID 699934-Methyloxybenzyl chlorideHCID 785483-Hydroxy-2,2-dimethylpropionic acid

Product 1

HCID 22035839HCID 22035839, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 1.03 g (8.7 mmol) of 2,2-dimethyl-3-hydroxypropionic acid, 1.8 mL (12.9 mmol), of TEA and 1.3 mL (9.5 mmol) of para-methoxybenzyl chloride in 8 mL of DME was stirred at rt for 24 h. The mixture was partitioned between 200 mL Et2O and 100 mL of H2O. After separating layers, the organic phase was washed with 100 mL of 1 N NaHCO3, 100 mL of 2 N HCl, 2×100 mL of H2O, 100 mL of brine, dried over MgSO4 and concentrated. The residue was purified by flash chromatography using a gradient of 3:1 v/v to 3:2 v/v of hexanes/EtOAc as the eluant to afford the title compound: RF: 0.17 (4:1 v/v hexanes/EtOAc); 1H-NMR (500 MHz) δ 1.21 (s, 6H), 3.57 (s, 2H), 3.82 (s, 3H), 5.09 (s, 2H), 6.90 (d, J=8.8, 2H), 7.28 (d, J=8.8, 2H).

Workup

  1. customThe mixture was partitioned between 200 mL Et2O and 100 mL of H2O
  2. customAfter separating layers
  3. washthe organic phase was washed with 100 mL of 1 N NaHCO3, 100 mL of 2 N HCl, 2×100 mL of H2O, 100 mL of brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-efaaf87c03804d8f87489e51e8076b6c
Source dataset
uspto-grants-2006_10
Patent number
US07125887B2

Reaction notes

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