Chlorosuccinimide → 4-[4-(1-Adamantyl)-2-chlorophenoxy]-butyric acid

HRID 1974200Notes

Reaction equation

HRID 1974200 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

HCID 31398ChlorosuccinimideHCID 214251534-[4-(1-Adamantyl)-phenoxy]butyric acid

Product 1

HCID 214251574-[4-(1-Adamantyl)-2-chlorophenoxy]-butyric acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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 an 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

  1. 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
  2. temperatureThe reaction solution is cooled to 0° C
  3. filtrationfiltered
  4. additiontreated with 40 ml of ice water
  5. customThe precipitate formed
  6. filtrationis filtered off
  7. washwashed with ice water
  8. customIt is then recrystallised twice from ethanol

Sources & evidence

ORD record
ord-c90910c2efb542419ba5719da91cc0c5
Source dataset
uspto-grants-1976_12
Patent number
US04000144

Reaction notes

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