4-Hydroxybenzaldehyde → 2-(4-Hydroxyphenyl)-1,3-dithiolane

HRID 1748977Notes

Reaction equation

HRID 1748977 reaction equation
O1CCCC1.B(F)(F)F.CCOCC.[OH:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=1.[CH2:24]([SH:27])[CH2:25][SH:26]>O.C(Cl)Cl>[S:26]1[CH2:25][CH2:24][S:27][CH:20]1[C:19]1[CH:22]=[CH:23][C:16]([OH:15])=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 8000Boron trifluoride etherateHCID 8028TetrahydrofuranHCID 109021,2-Ethanedithiol

Product 1

HCID 975622-(4-Hydroxyphenyl)-1,3-dithiolaneYield 108.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

In a tetrahydrofuran (THF) (3 mL) solvent, boron trifluoride diethyl etherate (0.03 mL, 0.25 mmol) was added to a mixed solution including 4-hydroxybenzaldehyde (300 mg, 2.16 mmol) and 1,2-ethanedithiol (0.21 mL, 2.46 mmol), and the reaction mixture was stirred at room temperature for 7 hours. The reaction mixture was distributed between methylene chloride and water, and an organic layer was dried by using MgSO4, filtered, and evaporated under reduced pressure to obtain Compound 81 (465 mg, 95.3%).

Workup

  1. customan organic layer was dried
  2. filtrationfiltered
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-c8e3e2618cbb49d6b04089eb08c652ea
Source dataset
uspto-grants-2015_10
Patent number
US09155690B2

Reaction notes

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