Chlorosuccinimide → 4-[4-(1-Adamantyl)-2-chlorophenoxy]-butyric acid
Reaction equation
[Cl:1]N1C(=O)CCC1=O.[C:9]12([C:19]3[CH:31]=[CH:30][C:22]([O:23][CH2:24][CH2:25][CH2:26][C:27]([OH:29])=[O:28])=[CH:21][CH:20]=3)[CH2:18][CH:13]3[CH2:14][CH:15]([CH2:17][CH:11]([CH2:12]3)[CH2:10]1)[CH2:16]2>CN(C)C=O>[Cl:1][C:30]1[CH:31]=[C:19]([C:9]23[CH2:10][CH:11]4[CH2:12][CH:13]([CH2:14][CH:15]([CH2:17]4)[CH2:16]2)[CH2:18]3)[CH:20]=[CH:21][C:22]=1[O:23][CH2:24][CH2:25][CH2:26][C:27]([OH:29])=[O:28]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
3.22 g of N-chlorosuccinimide are added to a solution of 7 g of 4-[4-(1-adamantyl)-phenoxy]-butyric acid in 40 ml of absolute dimethylformamide whilst stirring in a anhydrous atmosphere at 0° C. The mixture is then stirred for a further 15 minutes at 0° C, 30 minutes at about 25° C and 9 hours at 50° C. The reaction solution is cooled to 0° C, filtered and treated with 40 ml of ice water. The precipitate formed is filtered off and washed with ice water. It is then recrystallised twice from ethanol. 4-[2-Chloro-4-(1-adamantyl)-phenoxy]-butyric acid of melting point 164°-166° C is thus obtained.
Workup
- stirringThe mixture is then stirred for a further 15 minutes at 0° C, 30 minutes at about 25° C and 9 hours at 50° C
- temperatureThe reaction solution is cooled to 0° C
- filtrationfiltered
- additiontreated with 40 ml of ice water
- customThe precipitate formed
- filtrationis filtered off
- washwashed with ice water
- customIt is then recrystallised twice from ethanol
Sources & evidence
- ORD record
- ord-d722cd9c9cbb45408312c6e5b271d044
- Source dataset
- uspto-grants-1977_07
- Patent number
- US04035413
Reaction notes
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