4-Hydroxybenzoic Acid → 648422-76-8

HRID 72072Notes

Reaction equation

HRID 72072 reaction equation
O.[NH2:2][C:3]1[CH:8]=[C:7]([C:9]([CH3:13])([CH3:12])[CH2:10][CH3:11])[CH:6]=[CH:5][C:4]=1[OH:14].[OH:15][C:16]1[CH:24]=[CH:23][C:19]([C:20](O)=O)=[CH:18][CH:17]=1.B(O)(O)O>ClC1C=CC=CC=1Cl>[CH3:12][C:9]([C:7]1[CH:6]=[CH:5][C:4]2[O:14][C:20]([C:19]3[CH:23]=[CH:24][C:16]([OH:15])=[CH:17][CH:18]=3)=[N:2][C:3]=2[CH:8]=1)([CH3:13])[CH2:10][CH3:11]

Participants

6

Reactant 4

HCID 1354-Hydroxybenzoic AcidHCID 962Water2×HCID 7628Boric AcidHCID 3300422-Amino-4-tert-amylphenol

Product 1

HCID 136163370648422-76-8Yield 81.5%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

A 350 ml three necked reaction flask, equipped with a mechanical stirrer, a thermometer a “wood metal” heating bath and a reflux condenser combined with a water separator were charged with 25.1 g (140 mmol) of 2-amino-4-(1,1-dimethyl-propyl)-phenol (see above), 19.3 g (140 mmol) of 4-hydroxy benzoic acid and 1.5 g of boric acid suspended in 140 ml of 1,2-dichlorobenzene under nitrogen atmosphere. This mixture was refluxed until two equivalents of water had separated (about 4 hours). When cold, 50 ml of diisopropylether were added and this mixture was filtered and the crystalline product was washed with diisopropylether and pentane and dried. 32.1 g (81%) of the product were obtained. M.p. 236-237° C.

Workup

  1. temperaturea thermometer a “wood metal” heating bath and a reflux condenser
  2. customhad separated (about 4 hours)
  3. additionWhen cold, 50 ml of diisopropylether were added
  4. filtrationthis mixture was filtered
  5. washthe crystalline product was washed with diisopropylether and pentane
  6. customdried

Sources & evidence

ORD record
ord-c027ee709fac4a838a7b3ef6f1a06eef
Source dataset
uspto-grants-2014_09
Patent number
US08828365B2

Reaction notes

Loading…