Sodium Hydroxide → HCID 59606751, compound
Reaction equation
C(N(CC)C(=O)[O:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Cl:12])[C:7]=1[CH2:13][CH2:14][CH2:15][OH:16])C.[OH-].[Na+]>C(O)C>[Cl:12][C:8]1[C:7]([CH2:13][CH2:14][CH2:15][OH:16])=[C:6]([OH:5])[CH:11]=[CH:10][CH:9]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of the 3-chloro-2-(3-hydroxypropyl)phenyl diethylcarbamate (0.410 g; 1.43 mmol) in ethanol (14.5 ml) was added solid sodium hydroxide (0.144 g; 3.59 mmol) and the reaction mixture was heated at reflux for 21 h. After cooling, the volatiles were removed under reduced pressure, water was added and the mixture was extracted with diethyl ether, the combined organics were dried over magnesium sulphate, filtered and concentrated under reduced pressure. Purification by flash chromatography on silica gel using a gradient of ethyl acetate (15-100%) in heptane furnished 0.57 g (79%) of the desired 3-chloro-2-(3-hydroxypropyl)phenol.