Hydrochloric Acid → 3-Chloro-4-hydroxy-benzoic acid 2-methyl-butyl ester

HRID 1033702

Reaction equation

HRID 1033702 reaction equation
CC1C=CC(S(N(Cl)[Cl:12])(=O)=O)=CC=1.Cl.[CH3:15][CH:16]([CH2:28][CH3:29])[CH2:17][O:18][C:19](=[O:27])[C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1>C(O)(=O)C>[CH3:15][CH:16]([CH2:28][CH3:29])[CH2:17][O:18][C:19](=[O:27])[C:20]1[CH:21]=[CH:22][C:23]([OH:26])=[C:24]([Cl:12])[CH:25]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 68056Dichloramine-THCID 13530949Benzoic acid, 4-hydroxy-, 2-methylbutyl ester

Product 1

HCID 230416823-Chloro-4-hydroxy-benzoic acid 2-methyl-butyl esterYield 144.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

On the other hand, dichloramine T (28.0 g, 0.12 mol) was dissolved in acetic acid (450 ml), and hydrochloric acid (1.5 ml) was added. The resulting solution was dropwise added to a solution of the above p-hydroxybenzoic acid 2-methyl-butyl ester (50 g, 0.24 mol) dissolved in acetic acid (450 ml), followed by refluxing the mixture, allowing to stand overnight, distilling off acetic acid and filtering off deposited crystals to obtain 3-chloro-4-hydroxy-benzoic acid 2-methyl-butyl ester (42 g) (b.p. 135°~138° C./4 mmHg).

Workup

  1. temperatureby refluxing the mixture
  2. distillationdistilling off acetic acid
  3. filtrationfiltering off

Sources & evidence

ORD record
ord-9628d6e533e344f2897cf7d0226e1cb9
Source dataset
uspto-grants-1994_05
Patent number
US05312564

Linked notes

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