Hydrochloric Acid → [1,1'-Biphenyl]-2,6-diol

HRID 1511228Notes

Reaction equation

HRID 1511228 reaction equation
COC[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11]COC)[C:6]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.Cl.O>CO>[C:6]1([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:5]([OH:4])=[CH:10][CH:9]=[CH:8][C:7]=1[OH:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 251401012,6-Bis(methoxymethoxy)biphenyl

Product 1

HCID 15007745[1,1'-Biphenyl]-2,6-diolYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 16 (400 mg, 1.46 mmol) in MeOH (12.0 mL) at room temperature was treated dropwise with 3 M HCl (430 μL, 11.7 mmol), then heated to reflux for 1 hour. Water (15 mL) was added and the solution was extracted with EtOAc (3×20 mL). Combined organic fractions were washed with saturated aqueous NaCl, dried (Na2SO4), filtered, and concentrated to afford 17 as an orange amorphous solid (269 mg, 99%): 1H NMR (CDCl3, 400 MHz) 7.60 (d, J=7.6 Hz, 2H), 7.53-7.49 (m, 1H), 7.46-7.44 (m, 2H), 7.18 (t, J=8.2 Hz, 1H), 6.62 (d, J=8.2 Hz, 2H), 4.84 (s, 1H), 4.83 (s, 1H).

Workup

  1. temperatureheated
  2. temperatureto reflux for 1 hour
  3. extractionthe solution was extracted with EtOAc (3×20 mL)
  4. washCombined organic fractions were washed with saturated aqueous NaCl
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a60e543236cc4832b694d2de082ad370
Source dataset
uspto-grants-2012_07
Patent number
US08212011B2

Reaction notes

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