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

HRID 868476

Reaction equation

HRID 868476 reaction equation
ClNCl.[ClH:4].[CH3:5][CH:6]([CH2:18][CH3:19])[CH2:7][O:8][C:9](=[O:17])[C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1>C(O)(=O)C>[CH3:5][CH:6]([CH2:18][CH3:19])[CH2:7][O:8][C:9](=[O:17])[C:10]1[CH:11]=[CH:12][C:13]([OH:16])=[C:14]([Cl:4])[CH:15]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 76939ChlorimideHCID 13530949Benzoic acid, 4-hydroxy-, 2-methylbutyl ester

Product 1

HCID 230416823-Chloro-4-hydroxy-benzoic acid 2-methyl-butyl ester

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

On the other hand, dichloroamine 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-d758b38bf38540e5843d0f8742dd452f
Source dataset
uspto-grants-1988_10
Patent number
US04780242

Linked notes

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