Chlorobutanol → 4-Chloro-1-(naphthyloxy)-2-butanol
Reaction equation
[C:1]1([OH:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[OH-].[K+].Cl[CH2:15][CH:16]([OH:20])[CH2:17][CH2:18][Cl:19].CC(O)(C(Cl)(Cl)Cl)C>C(Cl)(Cl)Cl.O>[Cl:19][CH2:18][CH2:17][CH:16]([OH:20])[CH2:15][O:11][C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 65 °C
Procedure
To a mixture of 1 mole (147 g.) of 1-naphthol, 350 ml. of water and 2 moles (112 g.) of potassium hydroxide was added at 54° C. 1 mole (143 g.) of 1,4-dichloro-2-butanol. The temperature of the reaction mixture was kept below 60° C. during the addition of the chlorobutanol. The reaction mixture was heated at 65° C. for 12 hr., then mixed with 500 ml. of water and 350 ml. of chloroform. The chloroform layer was separated, washed with water, dried over sodium sulfate, concentrated and the residual oil distilled under reduced pressure to give 128 g. of a crystalline solid which was distilled at 162°-165° C./0.01 mm. The solid was recrystallized with ether and pet. ether (30°-60°) to give material melting at 75°-77° C.
Workup
- addition, then mixed with 500 ml
- customThe chloroform layer was separated
- washwashed with water
- dry with materialdried over sodium sulfate
- concentrationconcentrated
- distillationthe residual oil distilled under reduced pressure
- customto give 128 g
- distillationof a crystalline solid which was distilled at 162°-165° C./0.01 mm
- customThe solid was recrystallized with ether and pet. ether (30°-60°)
Sources & evidence
- ORD record
- ord-7d278ab332c24f4189e658561eb096b5
- Source dataset
- uspto-grants-1989_02
- Patent number
- US04806555
Reaction notes
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