2-methoxy-6-phenylmethoxybenzaldehyde

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of commercially available 2-hydroxy-6-methoxybenzaldehyde (1.000 g; 6.57 mmol), benzyl bromide (2.867 g; 16.43 mmol), and K2CO3 (2.960 g; 21.42 mmol) in anh. acetone (33 ml) was refluxed, under nitrogen, for 5.5 h. After cooling to rt, volatiles were removed under reduced pressure, and the residue was dissolved in water and AcOEt. The separated aq. layer was further extracted with AcOEt (2×), and the mixed organic layers were washed with brine, dried dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (heptane/AcOEt=8/2) afforded 2-(benzyloxy)-6-methoxybenzaldehyde. LC-MS (conditions E): tR=0.68 min.; [M+H]+: 243.27 g/mol. was refluxed, under nitrogen, for 5.5 h volatiles were removed under reduced pressure the residue was dissolved in water The separated aq. layer was further extracted with AcOEt (2×) the mixed organic layers were washed with brine dried dried over anh. MgSO4 filtered concentrated to dryness under reduced pressure Purification by FC (heptane/AcOEt=8/2)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of commercially available 2-hydroxy-6-methoxybenzaldehyde (1.000 g; 6.57 mmol), benzyl bromide (2.867 g; 16.43 mmol), and K2CO3 (2.960 g; 21.42 mmol) in anh. acetone (33 ml) was refluxed, under nitrogen, for 5.5 h. After cooling to rt, volatiles were removed under reduced pressure, and the residue was dissolved in water and AcOEt. The separated aq. layer was further extracted with AcOEt (2×), and the mixed organic layers were washed with brine, dried dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (heptane/AcOEt=8/2) afforded 2-(benzyloxy)-6-methoxybenzaldehyde. LC-MS (conditions E): tR=0.68 min.; [M+H]+: 243.27 g/mol. was refluxed, under nitrogen, for 5.5 h volatiles were removed under reduced pressure the residue was dissolved in water The separated aq. layer was further extracted with AcOEt (2×) the mixed organic layers were washed with brine dried dried over anh. MgSO4 filtered concentrated to dryness under reduced pressure Purification by FC (heptane/AcOEt=8/2)

Conditions: temp:240.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of commercially available 2-hydroxyisobutyramide (638.5 mg, 3 eq), 2-benzyloxy-6-methoxy-benzaldehyde (500 mg) (Katritzky A. R. et al ARKIVOC 2001, 2, 3, 3-12) is heated at 240° C. for 5 min using microwave irradiation (Lecolier S. et al Chimica Therapeutica 1969, 4,6, 437-445). The crude oil is poured into water and extracted with DCM. The combined organic extracts are dried (MgSO4), filtered and concentrated to yield a crude oil. FC (EN n-heptane: 1/1 to 1/0) gives the title compound as a yellow solid (0.41 g, 61%); LC-MS: tR=0.65 min; [M+H]+=328.22. microwave irradiation (Lecolier S. et al Chimica Therapeutica 1969, 4,6, 437-445) extracted with DCM The combined organic extracts are dried (MgSO4) filtered concentrated to yield a crude oil

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of commercially available 2-hydroxy-6-methoxybenzaldehyde (1.000 g; 6.57 mmol), benzyl bromide (2.867 g; 16.43 mmol), and K2CO3 (2.960 g; 21.42 mmol) in anh. acetone (33 ml) was refluxed, under nitrogen, for 5.5 h. After cooling to rt, volatiles were removed under reduced pressure, and the residue was dissolved in water and AcOEt. The separated aq. layer was further extracted with AcOEt (2×), and the mixed organic layers were washed with brine, dried dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (heptane/AcOEt=8/2) afforded 2-(benzyloxy)-6-methoxybenzaldehyde. LC-MS (conditions E): tR=0.68 min.; [M+H]+: 243.27 g/mol. was refluxed, under nitrogen, for 5.5 h volatiles were removed under reduced pressure the residue was dissolved in water The separated aq. layer was further extracted with AcOEt (2×) the mixed organic layers were washed with brine dried dried over anh. MgSO4 filtered concentrated to dryness under reduced pressure Purification by FC (heptane/AcOEt=8/2)