p-Toluenesulfonic acid monohydrate → HCID 15310388, compound

HRID 2069685Notes

Reaction equation

HRID 2069685 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[C:5]([CH2:10][C:11]([CH3:13])=[CH2:12])[CH:4]=1)[CH3:2].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(Cl)(Cl)Cl>[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]2[O:9][C:11]([CH3:13])([CH3:12])[CH2:10][C:5]=2[CH:4]=1)[CH3:2]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 22039021HCID 22039021, compound

Product 1

HCID 15310388HCID 15310388, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 4-ethyl-2-(2-methylallyl)phenol (812) (4 g, 22.7 mmol), p-toluenesulfonic acid monohydrate (400 mg, 2.10 mmol), and chloroform (120 mL) was stirred overnight at room temperature. The reaction was concentrated in vacuo, and purified by flash column chromatography on silica gel eluting with hexanes and ethyl acetate to give 5-ethyl-2,2-dimethyl-2,3-dihydrobenzofuran (813).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. custompurified by flash column chromatography on silica gel eluting with hexanes and ethyl acetate

Sources & evidence

ORD record
ord-30087130efef48efb737dd6d0e1b9d1f
Source dataset
uspto-grants-2012_10
Patent number
US08299117B2

Reaction notes

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