4-[3-Methoxy-4-(methoxymethoxy)phenyl]but-3-en-2-one → 4-(4-Hydroxy-3-methoxyphenyl)-3-buten-2-one
Reaction equation
COC[O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]=[CH:12][C:13](=[O:15])[CH3:14])=[CH:7][C:6]=1[O:16][CH3:17]>CO.Cl>[OH:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]=[CH:12][C:13](=[O:15])[CH3:14])=[CH:7][C:6]=1[O:16][CH3:17]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
1-(4-Methoxymethyloxy-3-methoxyphenyl)-1-buten-3-one (35j, 0.40 g, 1.7 mmol) was dissolved in methanol (40 ml) and stirred for 15 min at 50° C. Hydrochloric acid (3 drops) was added and the mixture stirred for 18 hr at 65° C. The methanol was evaporated and the resulting residue extracted into ethyl acetate, washed with saturated sodium chloride, dried over magnesium sulfate, filtered and evaporated to afford a solid. The crude solid was chromatographed on silica gel with ethyl acetate/hexane to give 0.24 g (74%) of an orange-yellow solid: mp 120-122° C. [expected mp 128-129° C.]; 1H NMR δ 2.34 (s, 3H), 3.91 (s, 3H), 5.98 (s, 1H), 6.56 (d, 1H, J=16.1 Hz), 6.91 (d, 1H, J=8.2 Hz), 7.04 (m, 2H), 7.43 (d, 1H, J=16.3 Hz); 13C NMR: δ 27.3, 56.0, 109.3, 114.8, 123.4, 124.9, 126.9, 143.6, 146.8, 148.2, 198.2.
Workup
- stirringthe mixture stirred for 18 hr at 65° C
- customThe methanol was evaporated
- extractionthe resulting residue extracted into ethyl acetate
- washwashed with saturated sodium chloride
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- customevaporated
- customto afford a solid
- customThe crude solid was chromatographed on silica gel with ethyl acetate/hexane
Sources & evidence
- ORD record
- ord-905278954149497fa7490135e49d8d80
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09187397B2
Reaction notes
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