Benzyl Bromide → 3-(4-Benzyloxyphenyl)-2-hydroxypropionic acid ethyl ester

HRID 1859941Notes

Reaction equation

HRID 1859941 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[OH:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH:23]([OH:29])[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:18][CH:17]=1>>[CH2:1]([O:15][C:16]1[CH:17]=[CH:18][C:19]([CH2:22][CH:23]([OH:29])[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:20][CH:21]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 21930973Ethyl p-hydroxyphenyllactate

Product 1

HCID 151861533-(4-Benzyloxyphenyl)-2-hydroxypropionic acid ethyl esterYield 96.9%

Conditions

Temperature
50 °C

Procedure

Benzyl bromide (21.9 g) and potassium carbonate (35.3 g) were added to a solution of ethyl 3-(4-hydroxyphenyl)lactate (22.4 g) in dimethylformnamide (220 ml). The mixture was stirred at 50° C. for 2 hours. The reaction mixture was partitioned between ethyl acetate and water. The ethyl acetate layer was separated and dried over magnesium sulfate and then concentrated under reduced pressure. The residue was purified via chromatography silica gel column using hexane/ethyl acetate=7/3 as the eluant to give the desired compound (31.0 g) as a pale yellow oil.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. customThe ethyl acetate layer was separated
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified via chromatography silica gel column

Sources & evidence

ORD record
ord-be8c11a1835a486585b5db781b7789e0
Source dataset
uspto-grants-2003_03
Patent number
US06528525B1

Reaction notes

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