Chloroacetone → 1-(2,6-Dimethylphenoxy)acetone

HRID 905531Notes

Reaction equation

Cl[CH2:2][C:3](=[O:5])[CH3:4].C1(C)CCC(C(C)C)[CH:8]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH:21]3C(C(C)C)CCC(C)C3)[C:16]=2[OH:31])C1>>[CH3:21][C:17]1[CH:18]=[CH:19][CH:20]=[C:15]([CH3:8])[C:16]=1[O:31][CH2:2][C:3](=[O:5])[CH3:4]

Participants

Reactant 2

HCID 6571Chloroacetone

HCID 54193089HCID 54193089, compound

Product 1

HCID 1043781-(2,6-Dimethylphenoxy)acetoneYield 84%

Procedure

Prepared by 1-chloro-propan-2-one (50 mmol) and 2,6-dimenthylphenol (60 mmol); purified by silica gel/hexane:ethyl acetate (5:1) column chromatography as a colorless oil; yield 84% (7.5 g); H NMR (400 MHz, CDCl3): d 2.34 (s, 6H, CH3), 2.42 (s, 3H, CH3), 4.40 (s, 2H, OCH2), 7.02-7.10 (m, 3H, Ar); CNMR (100 MHz, CDCl3): δ 16.3, 26.6, 76.8, 124.5, 129.1, 130.6, 155.0, 205.4; GC-MS m/z 178.1 (M+).

Workup

custompurified by silica gel/hexane

Sources & evidence

ORD record: ord-9e7d1bf7827f429f82b1d9523faae391
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08012901B1

Reaction notes

Loading…