Boric Acid → HCID 135725034, compound

HRID 2230163Notes

Reaction equation

HRID 2230163 reaction equation
[OH:1][C:2]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:3]=1[NH2:4].B(O)(O)O.[C:15]([C:19]1[CH:20]=[C:21]([CH:25]=[C:26]([C:29]([CH3:32])([CH3:31])[CH3:30])[C:27]=1[OH:28])[C:22](O)=O)([CH3:18])([CH3:17])[CH3:16]>C1(C)C(C)=CC=CC=1>[C:29]([C:26]1[CH:25]=[C:21]([C:22]2[O:1][C:2]3[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:3]=3[N:4]=2)[CH:20]=[C:19]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:27]=1[OH:28])([CH3:32])([CH3:31])[CH3:30]

Participants

5

Reactant 3

HCID 7628Boric AcidHCID 150073,5-Di-tert-butyl-4-hydroxybenzoic acidHCID 14191082-Amino-4-methoxyphenol

Product 1

HCID 135725034HCID 135725034, compoundYield 122.4%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of 2-hydroxy-5-methoxyaniline (36.9 mmole, 5.13 g), boric acid (36.9 mmole, 2.23 g) and 3,5-di-tert-butyl-4-hydroxybenzoic acid (36.9 mmole, 9.23 g) in xylene (550 ml) was refueled using a Dien Stark trap for approximately two days. The reaction mixture was then concentrated in vacuc to an oil. The oil was treated with ethyl acetate (200 ml) and washed with saturated aqueous sodium bicarbonate (3×200 ml). The organic phase was dried over sodium sulfate, filtered, and concentrated in vacuo to afford 15.96 g of a black oil. The material was subjected to preparatory chromatography eluting with 15 to 30% ethyl acetate: hexane over a 30 minute period. Fractions containing title compound were combined and concentrated in vacuo to afford 5.18 g of a solid.

Workup

  1. customfor approximately two days
  2. concentrationThe reaction mixture was then concentrated in vacuc to an oil
  3. additionThe oil was treated with ethyl acetate (200 ml)
  4. washwashed with saturated aqueous sodium bicarbonate (3×200 ml)
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-de0483fff8974a01b4a19888e26f5020
Source dataset
uspto-grants-2002_07
Patent number
US06423709B1

Reaction notes

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