Formaldehyde → HCID 59166221, compound

HRID 17945

Reaction equation

HRID 17945 reaction equation
OC1C=CC([CH2:8][C:9]#[N:10])=CC=1.[CH2:11]=[O:12].[OH2:13].[C:14]1([CH3:24])[CH:19]=[CH:18][C:17](S(O)(=O)=O)=[CH:16][CH:15]=1>C1(C)C=CC=CC=1>[O:12]1[C:15]2[CH:16]=[CH:17][C:18]([CH2:8][C:9]#[N:10])=[CH:19][C:14]=2[CH2:24][O:13][CH2:11]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 265484-Hydroxybenzyl cyanideHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 59166221HCID 59166221, compoundYield 9,757.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of (4-hydroxyphenyl)acetonitrile (17.3 g, 0.13 mol) in toluene (350 mL) were added paraformaldehyde (39.0 g, 0.43 mmol) and toluene-4-sulfonic acid monohydrate (2.5 g, 13 mmol) at room temperature. The reaction mixture was heated at reflux for 1 hour. Toluene was removed by evaporation. Water (150 mL) and ethyl acetate (150 mL) were added. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organics were washed with brine, dried over Na2SO4 and evaporated under vacuum. The residue was separated by preparative HPLC to give 2-(4H-benzo[d][1,3]dioxin-6-yl)acetonitrile (7.35 g, 32%). 1H NMR (400 MHz, CDCl3) δ 7.07-7.11 (m, 1H), 6.95-6.95 (m, 1H), 6.88 (d, J=11.6 Hz, 1H), 5.24 (s, 2H), 4.89 (s, 2H), 3.67 (s, 2H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 1 hour
  3. customToluene was removed by evaporation
  4. additionWater (150 mL) and ethyl acetate (150 mL) were added
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was extracted with ethyl acetate
  7. washThe combined organics were washed with brine
  8. dry with materialdried over Na2SO4
  9. customevaporated under vacuum
  10. customThe residue was separated by preparative HPLC

Sources & evidence

ORD record
ord-97fdd375e7ac4a87a776ef17a63e595e
Source dataset
uspto-grants-2010_06
Patent number
US07741321B2

Linked notes

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