Water → 2,5-Dipropylphenol

HRID 1816399Notes

Reaction equation

COC[O:4][C:5]1[CH:10]=[C:9]([CH2:11][CH2:12][CH3:13])[CH:8]=[CH:7][C:6]=1[CH:14](O)[CH2:15][CH3:16].C([SiH](CC)CC)C.FC(F)(F)C(O)=O.O>C(Cl)Cl>[CH2:14]([C:6]1[CH:7]=[CH:8][C:9]([CH2:11][CH2:12][CH3:13])=[CH:10][C:5]=1[OH:4])[CH2:15][CH3:16]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 1-[2-(methoxymethoxy)-4-propylphenyl]propan-1-ol (12.7 g, 53.3 mmol) and triethylsilane (21.3 mL, 133 mmol) in CH2Cl2 (120 mL) at 0° C. was added trifluoroacetic acid (16.4 mL, 213 mmol) slowly with an outlet needle attached to the round-bottom flask. The solution was stirred at 0° C. for 5 min and then at room temperature for 14 h. Water (40 mL) was added and the mixture was stirred at room temperature for 2 h. Extraction in CH2Cl2 (2×150 mL) with 50% saturated brine (5×100 mL) removed all of the trifluoroacetic acid. Flash chromatography with silica gel (gradient to 5% EtOAc/hexanes) furnished the title compound as a light green liquid (3.60 g, 38% yield): 1H NMR (300 MHz, CDCl3) δ 0.93 (t, 3H, J=7.3 Hz), 0.97 (t, 3H, J=7.3 Hz), 1.62 (m, 4H), 2.52 (m, 4H), 4.58 (s, 1H), 6.60 (s, 1H), 6.69 (d, 1H, J=7.6 Hz), 7.01 (d, 1H, J=7.6 Hz); MS m/e 179 (M+H)+.

Workup

waitat room temperature for 14 h
stirringthe mixture was stirred at room temperature for 2 h
extractionExtraction in CH2Cl2 (2×150 mL) with 50% saturated brine (5×100 mL)
customremoved all of the trifluoroacetic acid

Sources & evidence

ORD record: ord-55cd8fe246224455b3636235a91f5b50
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06884814B2

Reaction notes

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