2-butylphenol

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

Procedure: The procedure of Example 5 was repeated in all respects except 2-butylphenol was substituted for 4-t-butylphenol. 40% bleach number=0.5, 100% bleach number=4.

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

Procedure: To a mixture of methyl N-methylcarbamate (0.89 g, 0.01 mole) and 2-sec butylphenol (1.5 g, 0.01 mole) in dichloroethane (10 ml), a solution of phosphorus tribromide (2.7 g, 0.01 mole) in dichloro-ethane (6 ml) was added and the mixture was refluxed for eight hours. It was then worked up and purified as described earlier to give 2-sec butylphenyl N-methylcarbamate of the formula (III). the mixture was refluxed for eight hours purified

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

Procedure: To a mixture of methyl N-methylcarbamate (0.89 g, 0.01 mole) and 2-sec butylphenol (1.5 g, 0.01 mole) in dichloroethane (10 ml), a solution of phosphorus tribromide (2.7 g, 0.01 mole) in dichloro-ethane (6 ml) was added and the mixture was refluxed for eight hours. It was then worked up and purified as described earlier to give 2-sec butylphenyl N-methylcarbamate of the formula (III). the mixture was refluxed for eight hours purified

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

Procedure: To a solution of 2-sec butylphenol (1.5 g, 0.01 mole) and ethyl N-methylcarbamate (1.03 g, 0.01 mole), along with phosphorus pentachloride (1.05 g, 0.05 mole) in toluene (10 ml) was stirred at 28° C. and afterwards it was refluxed for 7 hours and worked up as usual to get the title compound. afterwards it was refluxed for 7 hours

Conditions: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-sec butylphenol (1.5 g, 0.01 mole) and ethyl N-methylcarbamate (1.03 g, 0.01 mole) was added phosphorus tribromide (2.7 g, 0.01 mole) and the contents were heated at 140° C. for 15 hours. The reaction mixture was worked up as described earlier to give 2-sec butylphenyl N-methylcarbamate, identified by spectral data.

Conditions: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-sec butylphenol (1.5 g, 0.01 mole) and ethyl N-methylcarbamate (1.03 g, 0.01 mole) was added phosphorus tribromide (2.7 g, 0.01 mole) and the contents were heated at 140° C. for 15 hours. The reaction mixture was worked up as described earlier to give 2-sec butylphenyl N-methylcarbamate, identified by spectral data.

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

Procedure: To a solution of 2-sec butylphenol (1.5 g, 0.01 mole) and ethyl N-methylcarbamate (1.03 g, 0.01 mole) in toluene (10 ml) at 60° C., phosphoryl chloride (0.77 g, 0.05 mole) was added dropwise during 0.5 hours and the contents refluxed for 5 hours. It was worked up as described earlier to furnish 2-sec butylphenyl N-methylcarbamate of the formula (III). the contents refluxed for 5 hours

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

Procedure: To a solution of 2-sec butylphenol (1.5 g, 0.01 mole) and ethyl N-methylcarbamate (1.03 g, 0.01 mole) in ethylene dichloride (6 ml) was added phosphoryl chloride (0.77 g, 0.05 mole) and the reaction mixture was refluxed under stirring for twenty hours. It was poured onto ice-cold water. The organic layer separated and aqueous layer was extracted with dichloroethane. The combined organic layer was washed with water, dried (Na2SO4) and distilled to give liquid residue, which was further purified by distillation to give 2-sec butyl N-methylcarbamate of the formula (III) [96% by GLC, DV-101 (3%), 150° C., nitrogen, 30 ml/min.] as a liquid, b.p. 110° C. (vap.)/4 mm; IR: 3320 (N--H), 1730 (--COO--), 1535,1490 and 750 (aromatic); PMR (CDCl3, 90 MHz): 0.81 (3H,t, primary methyl of side chain, 1.58 (2H, m, methylene protons of side chain), 2.88 (4H, doublet overlapping a multiplet, NH--CH3 and benzylic proton), 4.97 (1H, br s, N--H) and 6.95 to 7.25 (4H, m, aromatic). the reaction mixture was refluxed It was poured onto ice-cold water The organic layer separated aqueous layer was extracted with dichloroethane The combined organic layer was washed with water dried (Na2SO4) distilled to give liquid residue, which was further purified by distillation

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

Procedure: To a solution of 2-sec butylphenol (1.5 g, 0.01 mole) and ethyl N-methylcarbamate (1.03 g, 0.01 mole) in ethylene dichloride (6 ml) was added phosphoryl chloride (0.77 g, 0.05 mole) and the reaction mixture was refluxed under stirring for twenty hours. It was poured onto ice-cold water. The organic layer separated and aqueous layer was extracted with dichloroethane. The combined organic layer was washed with water, dried (Na2SO4) and distilled to give liquid residue, which was further purified by distillation to give 2-sec butyl N-methylcarbamate of the formula (III) [96% by GLC, DV-101 (3%), 150° C., nitrogen, 30 ml/min.] as a liquid, b.p. 110° C. (vap.)/4 mm; IR: 3320 (N--H), 1730 (--COO--), 1535,1490 and 750 (aromatic); PMR (CDCl3, 90 MHz): 0.81 (3H,t, primary methyl of side chain, 1.58 (2H, m, methylene protons of side chain), 2.88 (4H, doublet overlapping a multiplet, NH--CH3 and benzylic proton), 4.97 (1H, br s, N--H) and 6.95 to 7.25 (4H, m, aromatic). the reaction mixture was refluxed It was poured onto ice-cold water The organic layer separated aqueous layer was extracted with dichloroethane The combined organic layer was washed with water dried (Na2SO4) distilled to give liquid residue, which was further purified by distillation

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

Procedure: A solution of 30 parts of o-n-butylphenol in 150 parts of dry acetone was added dropwise over 5 hours to a stirred refluxing suspension of 80.8 parts of 1,3-dibromopropane, 27.6 parts of anydrous potassium carbonate and 0.5 parts of potassium iodide in 170 parts of dry acetone. refluxing

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

Procedure: A solution of 30 parts of o-n-butylphenol in 150 parts of dry acetone was added dropwise over 5 hours to a stirred refluxing suspension of 80.8 parts of 1,3-dibromopropane, 27.6 parts of anydrous potassium carbonate and 0.5 parts of potassium iodide in 170 parts of dry acetone. refluxing

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

Procedure: The procedure of Example 5 was repeated in all respects except 2-butylphenol was substituted for 4-t-butylphenol. 40% bleach number=0.5, 100% bleach number=4.