Water → Benzene, [(4-pentenyloxy)methyl]-

HRID 544411Notes

Reaction equation

HRID 544411 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:10](O)[CH2:11][CH2:12][CH:13]=[CH2:14].O>N1C=CC=CC=1>[CH2:1]([O:8][CH2:14][CH2:13][CH2:12][CH:11]=[CH2:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7412Benzoyl chlorideHCID 131814-Penten-1-OL

Product 1

HCID 10888453Benzene, [(4-pentenyloxy)methyl]-

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

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).

Workup

  1. customthe organic layer separated
  2. washThe product mixture was washed
  3. dry with materialThe organic layer was dried over anhydrous Na2CO3
  4. distillationthe product distilled

Sources & evidence

ORD record
ord-87bf83d0bba340dbaa16f5c50b38b46d
Source dataset
uspto-grants-1984_05
Patent number
US04450149

Reaction notes

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