p-Toluenesulfonic acid monohydrate → (5-Hydroxybenzofur-7-yl)acetonitrile

HRID 751485Notes

Reaction equation

HRID 751485 reaction equation
O1CCCCC1[O:7][C:8]1[CH:9]=[C:10]([CH2:17][C:18]#[N:19])[C:11]2[O:15][CH:14]=[CH:13][C:12]=2[CH:16]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[OH:7][C:8]1[CH:9]=[C:10]([CH2:17][C:18]#[N:19])[C:11]2[O:15][CH:14]=[CH:13][C:12]=2[CH:16]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 17985429[5-(Tetrahydropyran-2-yloxy)benzofur-7-yl]acetonitrile

Product 1

HCID 17985441(5-Hydroxybenzofur-7-yl)acetonitrileYield 96.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dissolve [5-(tetrahydropyran-2-yloxy)benzofur-7-yl]acetonitrile (3.89 g, 0.015 mol) in methanol (100 mL) and add para-toluene sulfonic acid monohydrate (0.288 g, 0.1 equivalent). After 20 minutes extract with ethyl acetate against water, then wash with brine. Concentration in vacuo affords 2.5 g (95.5%) of the title compound as an off-white solid. HRMS(m/z): Calcd 173.0465 Found 173.0477.

Workup

  1. extractionAfter 20 minutes extract with ethyl acetate against water
  2. washwash with brine
  3. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-083db5b0f2bc4a0b8cdd527dc8b19ba0
Source dataset
uspto-grants-2008_07
Patent number
US07405305B2

Reaction notes

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