(4-dodecoxyphenyl)methanol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: A solution of PBr3 (2.0 mL, 20 mmol) in anhydrous CH2Cl2 (25 mL) was added slowly to a stirred solution of 4-(dodecyloxy)benzyl alcohol (3.0 g, 10 mmol) in CH2Cl2 (50 mL) at 0° C. The reaction mixture was stirred for 3 h at room temperature and slowly poured into a large amount of water (ca. 600 mL). The product was extracted with CHCl3 (3×50 mL). The combined organic phase was washed with brine (3×20 mL), dried over anhydrous Na2SO4, and concentrated in vacuo to give a yellow solid (3.01 g, 90%). 1H NMR (300 MHz, CDCl3, δ): 7.32 (d, J=6.6 Hz, 2H), 6.86 (d, J=6.6 Hz, 2H), 4.50 (s, 2H), 3.97 (t, J=6.6 Hz, 2H), 4.05-4.00 (m, 6H), 1.79-1.72 (m, 2H), 1.45-1.21 (m, 12H), 0.90 (t, J=6.3 Hz, 3H). The product was extracted with CHCl3 (3×50 mL) The combined organic phase was washed with brine (3×20 mL) dried over anhydrous Na2SO4 concentrated in vacuo

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

Procedure: A solution of PBr3 (2.0 mL, 20 mmol) in anhydrous CH2Cl2 (25 mL) was added slowly to a stirred solution of 4-(dodecyloxy)benzyl alcohol (3.0 g, 10 mmol) in CH2Cl2 (50 mL) at 0° C. The reaction mixture was stirred for 3 h at room temperature and slowly poured into a large amount of water (ca. 600 mL). The product was extracted with CHCl3 (3×50 mL). The combined organic phase was washed with brine (3×20 mL), dried over anhydrous Na2SO4, and concentrated in vacuo to give a yellow solid (3.01 g, 90%). 1H NMR (300 MHz, CDCl3, δ): 7.32 (d, J=6.6 Hz, 2H), 6.86 (d, J=6.6 Hz, 2H), 4.50 (s, 2H), 3.97 (t, J=6.6 Hz, 2H), 4.05-4.00 (m, 6H), 1.79-1.72 (m, 2H), 1.45-1.21 (m, 12H), 0.90 (t, J=6.3 Hz, 3H). The product was extracted with CHCl3 (3×50 mL) The combined organic phase was washed with brine (3×20 mL) dried over anhydrous Na2SO4 concentrated in vacuo

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

Procedure: A solution of 4-(dodecyloxy)-benzaldehyde (10 g, 35 mmol) in THF (80 mL) was added dropwise to a stirred suspension of NaBH4 (2.7 g, 70 mmol) in dry THF (70 mL) at 0° C. The reaction mixture was stirred at room temperature overnight and was quenched with a small amount of water (5 mL). The solid formed was removed by filtration and the filtrate was concentrated in vacuo. The residue was dissolved in CHCl3 (50 mL). The resulting solution was washed with brine (3×20 mL), dried over anhydrous Na2SO4, and concentrated in vacuo to give a white powder (9.56 g, 94%). 1H NMR (400 MHz, CDCl3, δ): 7.29 (d, J=8.4 Hz, 2H), 6.90 (d, J=8.8 Hz, 2H), 4.62 (d, J=6.0 Hz, 2H), 3.97 (t, J=6.8 Hz, 2H), 1.79-1.51 (m, 2H), 1.51-1.26 (m, 19H), 0.90 (t, J=6.4 Hz, 3H). was quenched with a small amount of water (5 mL) The solid formed was removed by filtration the filtrate was concentrated in vacuo The residue was dissolved in CHCl3 (50 mL) The resulting solution was washed with brine (3×20 mL) dried over anhydrous Na2SO4 concentrated in vacuo

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: Thionyl chloride (38.8 g, 328 mmol) was added dropwise to a 0° C. solution of 4-Dodecyloxybenzyl alcohol (80.0 g, 274 mmol) in dry CH2Cl2 (900 mL) with a catalytic amount of DMF. Upon addition, reaction was allowed to stir for 5-10 minutes, while monitoring through TLC (CH2Cl2) for completion. Reaction mixture was concentrated under reduced pressure and the resulting residue re-crystallized from acetone to give the title benzyl chloride, decomposes upon melting. 77g (92%). Upon addition, reaction Reaction mixture was concentrated under reduced pressure the resulting residue re-crystallized from acetone

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

Procedure: Thionyl chloride (38.8 g, 328 mmol) was added dropwise to a 0° C. solution of 4-Dodecyloxybenzyl alcohol (80.0 g, 274 mmol) in dry CH2Cl2 (900 mL) with a catalytic amount of DMF. Upon addition, reaction was allowed to stir for 5-10 minutes, while monitoring through TLC (CH2Cl2) for completion. Reaction mixture was concentrated under reduced pressure and the resulting residue re-crystallized from acetone to give the title benzyl chloride, decomposes upon melting. 77g (92%). Upon addition, reaction Reaction mixture was concentrated under reduced pressure the resulting residue re-crystallized from acetone