ethyl 2-phenoxyacetate

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:

Conditions: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 3.8 g of methyl phenyl carbonate, 3.06 g of ethyl chloroacetate, and 0.42 g of TBPB was heated at 120° C. for 2 hours. Distillation of the resulting reaction mixture provided a 96 percent yield of ethyl phenoxyacetate. Distillation of the resulting reaction mixture

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

Procedure: Compound 34 (2 g, 0.011 mol) was dissolved in 100 mL of THF, and 1 M NaOH (110 mL, 0.11 mol) was added. The reaction mixture was stirred at RT for 24 h. The solution was then acidified by the addition of 40 mL of acetic acid. The reaction mixture was diluted with 150 mL of H2O and the product was extracted with ethyl acetate. The organic extracts were dried over magnesium sulfate and concentrated. The crude product was washed several times with hexane:ethylacetate (9:1) to give a pale white solid (1.58 g, 94%). 1H NMR (300 MHz, CD2Cl2) δ 4.69 (s, 2H), 6.92 (d, J=8.2 Hz, 2H), 7.03 (t, J=7.0 Hz, 1H), 7.32 (t, J=7.6 Hz, 2H). the product was extracted with ethyl acetate The organic extracts were dried over magnesium sulfate concentrated The crude product was washed several times with hexane:ethylacetate (9:1)

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

Procedure: The compound 34 was prepared according to the method described for compound 26 employing phenol (4.5 g, 0.05 mol), ethyl bromoacetate (31 g, 0.19 mol) and potassium carbonate (33 g, 0.24 mol) to give a colorless oily compound 34 (6.9 g, 81%). 1H NMR (300 MHz, CD2Cl2) δ 1.30 (t, J=7.0 Hz, 3H), 4.27 (q, J=7.0 Hz, 2H), 4.62 (s, 2H), 6.91 (d, J=7.9 Hz, 2H), 6.99 (t, J=7.0 Hz, 1H), 7.29 (t, J=7.6 Hz, 2H). The compound 34 was prepared

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

Procedure: Phenoxy-acetic acid ethyl ester (9.1 mL) is added to chlorosulfonic acid (15 mL) at 0° C. dropwise. The reaction is stirred at 0° C. for 30 min, it is allowed to warm to room temperature. After 2 hrs, the reaction mixture is poured into ice, solid product is collected by filtration and dried under vacuum. to warm to room temperature After 2 hrs the reaction mixture is poured into ice, solid product is collected by filtration dried under vacuum

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

Procedure: Phenoxy-acetic acid ethyl ester (9.1 mL) is added to chlorosulfonic acid (15 mL) at 0° C. dropwise. The reaction is stirred at 0° C. for 30 min, it is allowed to warm to room temperature. After 2 hrs, the reaction mixture is poured into ice, solid product is collected by filtration and dried under vacuum. to warm to room temperature After 2 hrs the reaction mixture is poured into ice, solid product is collected by filtration dried under vacuum

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 9.9 g of tert.-butyl 2,2-dimethyl-3-formyl-cyclopropane-carboxylate and 28 g of ethyl phenoxyacetate were added dropwise at 0° C. to a mixture of 0.05 ml of ethanol, 1.25 g of sodium in small pieces and 25 ml of toluene and the solution was stirred at 20° C. for 16 hours. 20 ml of toluene were added thereto and the mixture was stirred for 4 hours and was poured into iced water. The mixture was extracted with methylene chloride and the organic phase was evaporated to dryness under reduced pressure. The residue was chromatographed over silica gel and was eluted with a 7-3 hexane-ethyl acetate mixture to obtain 12.47 g of E or Z isomer of tert.-butyl (1R,trans) 2,2-dimethyl-3-[2-phenoxy-2-ethoxycarbonyl-ethenyl]-cyclopropane-carboxylate. the mixture was stirred for 4 hours The mixture was extracted with methylene chloride the organic phase was evaporated to dryness under reduced pressure The residue was chromatographed over silica gel was eluted with a 7-3 hexane-ethyl acetate mixture