HCID 68281404, compound → HCID 57385799, compound

HRID 1425935Notes

Reaction equation

HRID 1425935 reaction equation
CC1(C)C(C)(C)[O:5][B:4]([C:9]2[CH:14]=[C:13]([CH2:15][OH:16])[CH:12]=[CH:11][C:10]=2[CH2:17][OH:18])O1>Cl>[OH:16][CH2:15][C:13]1[CH:12]=[CH:11][C:10]2[CH2:17][O:18][B:4]([OH:5])[C:9]=2[CH:14]=1

Participants

3

Reactant 1

HCID 68281404HCID 68281404, compound

Product 1

HCID 57385799HCID 57385799, compoundYield 50.7%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

(2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1,4-phenylene)dimethanol (CVII) (2.0 g, 7.57 mmol) was dissolved in 6 M aqueous HCl (100 ml) at 60° C. and stirred overnight. The reaction mixture was concentrated under vacuum and the oily residue was triturated with Et2O to give a light-brown solid. The solid was removed by filtration and washed with Et2O. The filtrate (which according to LC/MS contained the product) was concentrated under vacuum to give 6-(hydroxymethyl)benzo[c][1,2]oxaborol-1(3H)-ol (CVIII) (0.63 g, 3.84 mmol, 35% purity). ESIMS found for C8H9BO3 m/z 163.0 (M−H). The crude product was used without further purification for Step 5.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. customthe oily residue was triturated with Et2O
  3. customto give a light-brown solid
  4. customThe solid was removed by filtration
  5. washwashed with Et2O
  6. concentrationwas concentrated under vacuum

Sources & evidence

ORD record
ord-74b9e03330f74e678d7d42ef215855d4
Source dataset
uspto-grants-2015_01
Patent number
US08933018B2

Reaction notes

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