Sulfuric Acid → Benzoic acid, 2-chloro-4-hydroxy-, 4-pentylphenyl ester

HRID 918551Notes

Reaction equation

HRID 918551 reaction equation
[CH2:1]([C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5].[Cl:13][C:14]1[CH:22]=[C:21]([OH:23])[CH:20]=[CH:19][C:15]=1[C:16](O)=[O:17].S(=O)(=O)(O)O.B(O)(O)O>C1(C)C=CC=CC=1>[Cl:13][C:14]1[CH:22]=[C:21]([OH:23])[CH:20]=[CH:19][C:15]=1[C:16]([O:12][C:9]1[CH:8]=[CH:7][C:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])=[CH:11][CH:10]=1)=[O:17]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 7628Boric AcidHCID 269754-PentylphenolHCID 918212-Chloro-4-hydroxybenzoic acid

Product 1

HCID 3084934Benzoic acid, 2-chloro-4-hydroxy-, 4-pentylphenyl ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of p-pentylphenol (0.15 mole) and 2-chloro-4-hydroxybenzoic acid (0.10 mole) in toluene (500 ml.) is added concentrated sulfuric acid (0.5 g.) and boric acid (0.31 g.) (5 mole percent). The reaction mixture is refluxed for 29 hours under a Dean-Stark trap. The solvent is then removed under reduced pressure and the product is washed with ligroin. The resulting 4-pentylphenyl 2-chloro-4-hydroxybenzoate is recrystallized from an ethanol/water mixture to give 25.6 g., 81% of pure product, m.p. 149°-151°C.

Workup

  1. temperatureThe reaction mixture is refluxed for 29 hours under a Dean-Stark trap
  2. customThe solvent is then removed under reduced pressure
  3. washthe product is washed with ligroin
  4. customThe resulting 4-pentylphenyl 2-chloro-4-hydroxybenzoate is recrystallized from an ethanol/water mixture
  5. customto give 25.6 g

Sources & evidence

ORD record
ord-57f01a4ad51941caaf854eb1358aa1de
Source dataset
uspto-grants-1976_07
Patent number
US03971824

Reaction notes

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