pent-4-enoxymethylbenzene

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

Procedure: 5-Benzoxy-1-pentene (30 mmol, 5.7 g) was hydroborated with BH3 -THF (10 mmol) at 0° C. for 1 hr. Iodinemonochloride (20 mmol, 1.0 ml) was added at room temperature; after 45 min,the product was isolated via chromatography (alumina): yield 5.63 g (88% based on ICl); bp 125° C./0.25 torr; m/e 318.1 (Calcd 318.2); IR (neat) 1705(C=O), 1205(C-I)cm-1 ; NMR (neat) δ 1.7 (broad envelope, 6, alkyl), 3.0 (t, 2, --CH2I), 4.2 (t, 2, --CH2O--),7.6 (m, 5, ArH). at 0° C. for 1 hr the product was isolated via chromatography (alumina)

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

Procedure: Benzoyl chloride (0.2 mol, 23 ml) was added dropwise to a solution of 4penten-1-ol (0.2 mol, 20 ml) in pyridine and stirred overnight at room temperature. The reaction mixture was poured into 100 mlof water and the organic layer separated. The product mixture was washed, sequentially, with dilute HCl, saturated aqueous Na2CO3, and water. The organic layer was dried over anhydrous Na2CO3 and the product distilled: bp 90°-98° (1.0 mmHg); yield 26.9g, (71%); NMR (neat) δ 1.5 (broad m, 4, alkyl), 3.8 (t, 2, --OCH2 --), 4.6 (m, 2, =CH2), 5.2 (m, 1, =CH--), 7.3 (m, 5, ArH). the organic layer separated The product mixture was washed The organic layer was dried over anhydrous Na2CO3 the product distilled

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

Procedure: 5-Benzoxy-1-pentene (30 mmol, 5.7 g) was hydroborated with BH3 -THF (10 mmol) at 0° C. for 1 hr. Iodinemonochloride (20 mmol, 1.0 ml) was added at room temperature; after 45 min,the product was isolated via chromatography (alumina): yield 5.63 g (88% based on ICl); bp 125° C./0.25 torr; m/e 318.1 (Calcd 318.2); IR (neat) 1705(C=O), 1205(C-I)cm-1 ; NMR (neat) δ 1.7 (broad envelope, 6, alkyl), 3.0 (t, 2, --CH2I), 4.2 (t, 2, --CH2O--),7.6 (m, 5, ArH). at 0° C. for 1 hr the product was isolated via chromatography (alumina)

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

Procedure: Benzoyl chloride (0.2 mol, 23 ml) was added dropwise to a solution of 4penten-1-ol (0.2 mol, 20 ml) in pyridine and stirred overnight at room temperature. The reaction mixture was poured into 100 mlof water and the organic layer separated. The product mixture was washed, sequentially, with dilute HCl, saturated aqueous Na2CO3, and water. The organic layer was dried over anhydrous Na2CO3 and the product distilled: bp 90°-98° (1.0 mmHg); yield 26.9g, (71%); NMR (neat) δ 1.5 (broad m, 4, alkyl), 3.8 (t, 2, --OCH2 --), 4.6 (m, 2, =CH2), 5.2 (m, 1, =CH--), 7.3 (m, 5, ArH). the organic layer separated The product mixture was washed The organic layer was dried over anhydrous Na2CO3 the product distilled