(+)-Epichlorohydrin → (R)-1-chloro-3-(3-(2-ethylbutoxy)phenyl)propan-2-ol

HRID 882431

Reaction equation

Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH2:9][CH:10]([CH2:13][CH3:14])[CH2:11][CH3:12])[CH:3]=1.[CH2:15]([C@H:17]1[O:19][CH2:18]1)[Cl:16]>>[Cl:16][CH2:15][C@H:17]([OH:19])[CH2:18][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH2:9][CH:10]([CH2:13][CH3:14])[CH2:11][CH3:12])[CH:3]=1

Participants

Reactant 2

HCID 149428(+)-Epichlorohydrin

HCID 673177401-Bromo-3-(2-ethylbutoxy)benzene

Product 1

HCID 67316767(R)-1-chloro-3-(3-(2-ethylbutoxy)phenyl)propan-2-ol

Procedure

Metallation of 1-bromo-3-(2-ethylbutoxy)benzene followed by addition to (S)-(+)-epichlorohydrin gave (R)-1-chloro-3-(3-(2-ethylbutoxy)phenyl)propan-2-ol. Yield (1.55 g, 59%): 1H NMR (400 MHz, DMSO-d6) δ 7.14 (t, J=7.8 Hz, 1H), 6.77-6.72 (m, 3H), 5.13 (d, J=4.8 Hz, 1H), 3.88-3.82 (m, 1H), 3.78 (d, J=5.6 Hz, 2H), 3.52 (dd, J=10.8, 4.4 Hz, 1H), 3.43 (dd, J=10.8, 5.6 Hz, 1H), 2.74 (dd, J=13.6, 5.2 Hz, 1H), 2.61 (dd, J=13.2, 7.4 Hz, 1H), 1.74-1.69 (m, 1H), 1.39-1.25 (m, 8H), 0.85 (t, J=7.0 Hz, 6H).

Sources & evidence

ORD record: ord-8501232e57ba43a0ae124fa32676a7f1
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08993807B2

Linked notes

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