Isopropanol → HCID 22338345, compound

HRID 931406Notes

Reaction equation

C([O:8][CH2:9][CH2:10][CH2:11][C:12](O)=[O:13])C1C=CC=CC=1.S(Cl)(Cl)=O.[CH3:19][CH:20]([OH:22])[CH3:21]>>[OH:13][CH2:12][CH2:11][CH2:10][C:9]([O:22][CH:20]([CH3:21])[CH3:19])=[O:8]

Participants

Reactant 3

HCID 3776Isopropanol

HCID 24386Thionyl Chloride

HCID 5622014-(Benzyloxy)butanoic acid

Product 1

HCID 22338345HCID 22338345, compound

Procedure

To a solution of 4-benzyloxybutyric acid (20.59 mmol) in propan-2-ol (30 mL) under nitrogen at 0° C. was added dropwise thionyl chloride (22.65 mmol). The reaction mixture was allowed to reach room temperature over 30 minutes and stirred at room temperature during 20 hours. The mixture was concentrated under reduced pressure and co-evaporated with CH2Cl2. The crude was dried under vacuum pump to give the expected compound as yellow oil in quantitative yield. 1H NMR (CDCl3, 400 MHz) δ (ppm) 1.22 (d, J=6.26 Hz, 6H), 1.94 (quintuplet, J=6.70 Hz, 2H), 2.40 (t, J=7.47 Hz, 2H), 3.50-3.53 (m, 2H), 4.51 (s, 2H), 5 (heptuplet, J=6.22 Hz, 1H), 7.28-7.38 (m, 5H); MS (ESI) m/z=259.6 (MNa+).

Workup

concentrationThe mixture was concentrated under reduced pressure and co-evaporated with CH2Cl2
customThe crude was dried under vacuum pump

Sources & evidence

ORD record: ord-f24ec6decf28450195cfabb981df6e0d
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296778B2

Reaction notes

Loading…