Hydrochloric Acid → 3,3,6-trimethylbenzo[c][1,2]oxaborol-1(3H)-ol

HRID 1037074Notes

Reaction equation

HRID 1037074 reaction equation
C(OCOC([C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][C:10]=1[B:16]1[O:20][C:19]([CH3:22])([CH3:21])C(C)(C)[O:17]1)(C)C)C.Cl>C1COCC1>[CH3:22][C:19]1([CH3:21])[O:20][B:16]([OH:17])[C:10]2[CH:11]=[C:12]([CH3:15])[CH:13]=[CH:14][C:9]1=2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 866855182-(2-(2-(Ethoxymethoxy)propan-2-yl)-5-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 866854553,3,6-trimethylbenzo[c][1,2]oxaborol-1(3H)-olYield 51.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of compound 2-(2-(2-(ethoxymethoxy)propan-2-yl)-5-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (76.2 mmol) in THF (100 mL) was added 6 N HCl (381 mL). The reaction mixture was stirred at rt overnight, and the obtained mixture was extracted three times with ethyl acetate. The combined extracts were washed with water and brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography over silica gel eluted with PE-EA (20:1) to give 3,3,6-trimethylbenzo[c][1,2]oxaborol-1(3H)-ol (6.87 g; yield 51.2% over 2 steps) as a white solid. MS: m/z=177.1 (M+1, ESI+).

Workup

  1. extractionthe obtained mixture was extracted three times with ethyl acetate
  2. washThe combined extracts were washed with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography over silica gel
  7. washeluted with PE-EA (20:1)

Sources & evidence

ORD record
ord-9190e62866e146bdae46ed8e5d66f050
Source dataset
uspto-grants-2013_10
Patent number
US08546357B2

Reaction notes

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