Ethanol → (2S)-3-(4-hydroxy-phenyl)-2-methoxypropionic acid ethyl ester

HRID 459265Notes

Reaction equation

HRID 459265 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@H:9]([O:13][CH3:14])[C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH2:20](O)[CH3:21]>>[CH3:14][O:13][C@@H:9]([CH2:8][C:5]1[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=1)[C:10]([O:12][CH2:20][CH3:21])=[O:11]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 11564639(2S)-3-(4-hydroxyphenyl)-2-methoxypropanoic acid

Product 1

HCID 11390460(2S)-3-(4-hydroxy-phenyl)-2-methoxypropionic acid ethyl ester

Procedure

A solution of (2S)-3-(4-hydroxyphenyl)-2-methoxypropanoic acid (35 g) in 140 ml of ethanol was mixed with 5.66 ml of concentrated sulfuric acid and stirred at room temperature until complete as indicated by HPLC. The ethanol was removed via vacuum distillation (55° C./28″Hg) and 110 ml of water was added. The pH was adjusted to about 7 to 8 with sodium bicarbonate, and the mixture was extracted with add 50 ml ethyl acetate (3×50 ml). The organic layers were combined, washed with 50 ml 20% NaCl solution, dried with 15 g of magnesium sulfate, and concentrate product to afford ethyl (2S)-2-methoxy-3-(4-hydorxyphenyl)propanoate as an oil. 1H-NMR (CDCl3): 7.1 (d, 2H); 6.7(d, 2H); 4.2(m, 2H); 3.9(m, 1H); 3.6(s, 3H); 2.95(m, 2H); 1.25(t, 3H). MS (ES): 223.2 (M−1).

Workup

  1. customThe ethanol was removed via vacuum distillation (55° C./28″Hg) and 110 ml of water
  2. additionwas added
  3. extractionthe mixture was extracted
  4. additionwith add 50 ml ethyl acetate (3×50 ml)
  5. washwashed with 50 ml 20% NaCl solution
  6. dry with materialdried with 15 g of magnesium sulfate
  7. concentrationconcentrate product

Sources & evidence

ORD record
ord-aec32a0454fb4b6baf79b455088be0fe
Source dataset
uspto-grants-2007_03
Patent number
US07192982B2

Reaction notes

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