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

HRID 459299Notes

Reaction equation

HRID 459299 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]>>[CH2:20]([O:11][C:10](=[O:12])[C@@H:9]([O:13][CH3:14])[CH2:8][C:5]1[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=1)[CH3:21]

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

The compound of (2S)-3-(4-hydroxy-phenyl)-2-methoxy-propionic acid (5.1 mmol) was dissolved in 50 ml of ethanol and 0.3 ml (5.6 mmol) of sulfuric acid was added. The mixture was stirred at room temperature for 18 hours and then concentrated. The mixture was diluted with water (55 ml) and NaHCO3 was added (310 mg, 3.7 mmol). This mixture was extracted with ethyl acetate (4×20 mL), and the combined organic layers were dried (MgSO4) and then concentrated to produce a yellow oil. 1H-NMR (CDCl3, 200.15 MHz): 7.07 (d, 2H, J=8.6), 6.72 (d, 2H, J=8.6), 5.42 (br s, 1H), 4.18 (q, 2H, J=7.3), 3.92 (dd, 1H, J=6.7, 5.9), 3.36 (s, 3H), 2.95 (d, 2H, J=6.7), 1.23 (t, 3H, J=7.3).

Workup

  1. concentrationconcentrated
  2. additionThe mixture was diluted with water (55 ml) and NaHCO3
  3. additionwas added (310 mg, 3.7 mmol)
  4. extractionThis mixture was extracted with ethyl acetate (4×20 mL)
  5. dry with materialthe combined organic layers were dried (MgSO4)
  6. concentrationconcentrated
  7. customto produce a yellow oil

Sources & evidence

ORD record
ord-c5ec3cdf591c4a478bf6eda26ac0ae8c
Source dataset
uspto-grants-2007_03
Patent number
US07192982B2

Reaction notes

Loading…