tert-Butanol → 1-(1-Chloro-3-methyl-naphthalen-2-yl)-ethane-1,2-diol

HRID 926197Notes

Reaction equation

[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4](C)[C:3]=1C=C.S([O-])([O-])=[O:16].[Na+].[Na+].[C:21]([OH:25])(C)([CH3:23])[CH3:22]>ClCCl.O>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([CH3:3])[C:22]=1[CH:21]([OH:25])[CH2:23][OH:16]

Participants

Conditions

Temperature: 0 °C

Procedure

A biphasic mixture of AD mix-α (6.907 g) in tert-butanol (24.5 mL)/H2O (24.5 mL) was cooled to 0° C. and 1-chloro-3-methyl-2-vinyl-naphthalene (1.00 g, 4.93 mmol) was added. The reaction mixture was stirred for 8 h at 0° C. Sodium sulfite (7.4 g) was added at 0° C. and the reaction was stirred for 40 minutes to give a white mixture. The mixture was diluted with dichloromethane and H2O. The mixture was extracted with dichloromethane (3×) and the combined organic layer was dried (MgSO4), filtered, concentrated and purified by flash column chromatography (silica gel, 0 to 100% ethyl acetate/hexanes) to give 1-(1-chloro-3-methyl-naphthalen-2-yl)-ethane-1,2-diol. 1H NMR (400 MHz, CDCl3) δ 8.27 (d, J=8.2 Hz, 1H), 7.72 (d, J=7.8 Hz, 1H), 7.57 (s, 1H), 7.56-7.47 (m, 2H), 5.70 (dd, J=9.4, 3.9 Hz, 1H), 4.11 (dd, J=10.5, 10.5 Hz, 1H), 3.80 (dd, J=11.6, 3.9 Hz, 1H), 2.66 (s, 3H).

Workup

stirringthe reaction was stirred for 40 minutes
customto give a white mixture
extractionThe mixture was extracted with dichloromethane (3×)
dry with materialthe combined organic layer was dried (MgSO4)
filtrationfiltered
concentrationconcentrated
custompurified by flash column chromatography (silica gel, 0 to 100% ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-7904829a49a242f6b99b0afa8dd5a37a
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09284323B2

Reaction notes

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