Isopropanol → Propan-2-yl 3-hydroxypropanoate

HRID 931405Notes

Reaction equation

HRID 931405 reaction equation
C([O:8][CH2:9][CH2:10][C:11](O)=[O:12])C1C=CC=CC=1.S(Cl)(Cl)=O.[CH3:18][CH:19]([OH:21])[CH3:20]>C(Cl)Cl>[OH:12][CH2:11][CH2:10][C:9]([O:21][CH:19]([CH3:20])[CH3:18])=[O:8]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 24386Thionyl ChlorideHCID 156088133-(Benzyloxy)propanoic acid

Product 1

HCID 12847346Propan-2-yl 3-hydroxypropanoateYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-benzyloxypropanoic acid (27.7 mmol) in propan-2-ol (40 mL) under nitrogen at 0° C. was added dropwise thionyl chloride (30.5 mmol). The reaction mixture was allowed to reach room temperature over 30 minutes and stirred at room temperature overnight. The mixture was diluted with CH2Cl2 and washed with a saturated solution of NaHCO3 and brine. The organic layer was dried on Na2SO4, filtered and concentrated under reduced pressure. The crude was diluted with isopropanol (80 mL) and Pd(OH)2 (20%, 1 g) in isopropanol was added. The system (reaction in a stainless steel reactor) was purged with nitrogen, vacuum and H2 and the reaction mixture was stirred under H2 atmosphere (3 bars) overnight at room temperature. The reaction mixture was filtered through autocup and the precipitate was washed with isopropanol. The filtrates were concentrated under reduced pressure and dried under vacuum pump to give the expected compound in 78% yield. 1H NMR (CDCl3, 400 MHz) δ (ppm) 1.26 (d, J=6.31 Hz, 6H), 2.19 (brs, 1H), 2.54 (t, J=5.56 Hz, 2H), 3.86 (t, J=5.56 Hz, 2H), 5.06 (heptuplet, J=6.25 Hz, 1H).

Workup

  1. washwashed with a saturated solution of NaHCO3 and brine
  2. customThe organic layer was dried on Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. additionThe crude was diluted with isopropanol (80 mL) and Pd(OH)2 (20%, 1 g) in isopropanol
  6. additionwas added
  7. customThe system (reaction in a stainless steel reactor)
  8. customwas purged with nitrogen, vacuum and H2
  9. stirringthe reaction mixture was stirred under H2 atmosphere (3 bars) overnight at room temperature
  10. filtrationThe reaction mixture was filtered through autocup
  11. washthe precipitate was washed with isopropanol
  12. concentrationThe filtrates were concentrated under reduced pressure
  13. customdried under vacuum pump

Sources & evidence

ORD record
ord-fbe1e757922946498f2770a876d17fe4
Source dataset
uspto-grants-2016_03
Patent number
US09296778B2

Reaction notes

Loading…