Benzyl Alcohol → HCID 58292850, compound

HRID 1798139Notes

Reaction equation

HRID 1798139 reaction equation
[OH:1][B:2]1[C:6]2[CH:7]=[C:8]([OH:12])[CH:9]=[C:10]([CH3:11])[C:5]=2[CH:4]([CH2:13][C:14]([OH:16])=[O:15])[O:3]1.[CH3:17][C:18]1[CH:23]=[CH:22][C:21](S(O)(=O)=O)=[CH:20][CH:19]=1.C(O)C1C=CC=CC=1>C1(C)C=CC=CC=1>[OH:1][B:2]1[C:6]2[CH:7]=[C:8]([OH:12])[CH:9]=[C:10]([CH3:11])[C:5]=2[CH:4]([CH2:13][C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[O:3]1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 6101p-Toluenesulfonic acidHCID 582927912-(1,6-Dihydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetic acid

Product 1

HCID 58292850HCID 58292850, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 2-(1,6-dihydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetic acid (400 mg, 1.8 mmol) in 30 mL toluene was added 4-methylbenzenesulfonic acid (68.5 mg, 0.36 mmol) and BnOH (583.8 mg, 5.4 mmol). The reaction mixture was refluxed for 5 h and concentrated to dryness. The residue was dissolved in 20 mL EtOAc and washed with H2O (15 mL). The aqueous layer was extracted with EtOAc (2×20 mL). The combined organic layers were dried with anhydrous Na2SO4 and concentrated to dryness. The residue was used directly in next step reaction without further purification.

Workup

  1. temperatureThe reaction mixture was refluxed for 5 h
  2. concentrationconcentrated to dryness
  3. dissolutionThe residue was dissolved in 20 mL EtOAc
  4. washwashed with H2O (15 mL)
  5. extractionThe aqueous layer was extracted with EtOAc (2×20 mL)
  6. dry with materialThe combined organic layers were dried with anhydrous Na2SO4
  7. concentrationconcentrated to dryness
  8. customThe residue was used directly in next step reaction without further purification

Sources & evidence

ORD record
ord-b495641ff8b54470ab97e4b398e5a39f
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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