methyl 2-[4-(hydroxymethyl)-2-methoxyphenoxy]acetate

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 (4-Hydroxymethyl-2-methoxy-phenoxy)-acetic acid methyl ester 72 (40 grams, 177 mmol), Acetic anhydride (80 mL) and pyridine (4 mL) was refluxed for 4 hours. Reaction mixture was poured in to ice water (200 mL) and crude 73 was extracted into chloroform, dried over Na2SO4, and distilled. The crude was vacuum distilled to give pure 73 (30 grams, 64%) as a color less liquid, Bp15 210° C. The structure was confirmed with IR and NMR. IHNMR (CDCl3) δ 2.08 (s, 3H,O═C—CH3), 3.78(s, 3H,ester), 3.90(s, 3H, OCH3), 4.65(s, 2H,OCH2), 5.00 (s, 2H, CH2), 6.76(d,1H,Ar), 6.80 (d, 2H,Ar), 6.85 (dd,1H,Ar). Reaction mixture was extracted into chloroform dried over Na2SO4 distilled distilled

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of (4-Formyl-2-methoxy-phenoxy)acetic acid methyl ester 71 (50 grams, 223 mmol) in methanol (500 mL) at 0° C. was added Sodium boro hydrate (4 grams, 106 mmol) in small portions, further stirred at 0° C. for 30 minutes and poured on to ice water (200 mL). The pH of mixture was adjusted to 2 with concentrated hydrochloric acid. Crude 72 was extracted into chloroform, dried over Na2SO4 and distilled to give 72 (40 grams, 62%) as a light yellow syrup. Crude 72 was extracted into chloroform dried over Na2SO4 distilled

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

Procedure: A solution of (4-Hydroxymethyl-2-methoxy-phenoxy)-acetic acid methyl ester 72 (40 grams, 177 mmol), Acetic anhydride (80 mL) and pyridine (4 mL) was refluxed for 4 hours. Reaction mixture was poured in to ice water (200 mL) and crude 73 was extracted into chloroform, dried over Na2SO4, and distilled. The crude was vacuum distilled to give pure 73 (30 grams, 64%) as a color less liquid, Bp15 210° C. The structure was confirmed with IR and NMR. IHNMR (CDCl3) δ 2.08 (s, 3H, O═C—CH3), 3.78 (s, 3H, ester), 3.90 (s, 3H, OCH3), 4.65 (s, 2H, OCH2), 5.00 (s, 2H, CH2), 6.76 (d, 1H, Ar), 6.80 (d, 2H, Ar), 6.85 (dd, 1H, Ar). Reaction mixture was extracted into chloroform dried over Na2SO4 distilled distilled

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of (4-Formyl-2-methoxy-phenoxy)acetic acid methyl ester 71 (50 grams, 223 mmol) in methanol (500 mL) at 0° C. was added Sodium boro hydrate (4 grams, 106 mmol) in small portions, further stirred at 0° C. for 30 minutes and poured on to ice water (200 mL). The pH of mixture was adjusted to 2 with concentrated hydrochloric acid. Crude 72 was extracted into chloroform, dried over Na2SO4 and distilled to give 72 (40 grams, 62%) as a light yellow syrup. Crude 72 was extracted into chloroform dried over Na2SO4 distilled