M-Cresol → HCID 19895386, compound

HRID 2281936Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.FC(F)(F)S(O)(=O)=O.[C:17](Cl)(=[O:20])[CH2:18][CH3:19]>>[OH:8][C:4]1[CH:5]=[CH:6][C:7]([C:17](=[O:20])[CH2:18][CH3:19])=[C:2]([CH3:1])[CH:3]=1

Participants

Reactant 3

HCID 342M-Cresol

HCID 62324Propionyl chloride

HCID 62406Trifluoromethanesulfonic acid

Product 1

HCID 19895386HCID 19895386, compound

Conditions

Temperature: -10 °C

Procedure

3-Methylphenol (9.0 g, 83 mmol) was combined with trifluoromethanesulfonic acid (90 mL), cooled to −10° C., and treated in a drop-wise manner with propanoyl chloride (7.7 g, 83 mmol). The reaction mixture was stirred at −10° C. for 3 hours and then at room temperature for 18 hours, whereupon it was poured into ice water (600 mL). The resulting solid was collected via filtration and purified by silica gel chromatography (Gradient: 5% to 70% ethyl acetate in petroleum ether) to afford the product as an off-white solid. Yield: 6.7 g, 41 mmol, 49%. 1H NMR (400 MHz, CD3OD) δ 7.75 (d, J=8.5 Hz, 1H), 6.64-6.69 (m, 2H), 2.92 (q, J=7.3 Hz, 2H), 2.45 (s, 3H), 1.13 (t, J=7.3 Hz, 3H).

Workup

waitat room temperature for 18 hours
filtrationThe resulting solid was collected via filtration
custompurified by silica gel chromatography (Gradient: 5% to 70% ethyl acetate in petroleum ether)

Sources & evidence

ORD record: ord-7e2dd64676f44c60a4725947d75f7a0e
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09139561B2

Reaction notes

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