Sodium Cyanide → 3-Cyano-4-hydroxybenzoic acid

HRID 710404Notes

Reaction equation

HRID 710404 reaction equation
I[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11]CCC)[C:5]([OH:7])=[O:6].[C-]#N.[Na+].[C:18]([Cu])#[N:19]>CN(C=O)C>[C:18]([C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[OH:11])[C:5]([OH:7])=[O:6])#[N:19]

Participants

5

Reactant 3

HCID 8929Sodium CyanideHCID 448288973-Iodo-4-propoxybenzoic acidHCID 178418546HCID 178418546, compound

Product 1

HCID 111374633-Cyano-4-hydroxybenzoic acidYield 85.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of the product of Example 44 Step C (0.22 g; 0.72 mmol), NaCN (0.04 g; 0.8 mmol) and CuCN (0.07 g; 0.8 mmol) in anhydrous DMF (2 ml) was stirred at ˜110° C. for 2 h under N2. This was evaporated to dryness in vacuo and the residue was suspended in H2O (10 ml) and pH was adjusted to ˜10 with 1 M NaOH. The insoluble material was removed by filtration and the filtrate was acidified to pH˜3 with diluted HCl and the product was taken up by CH2Cl2 (2×20 ml). The organic phase was dried over anhydrous MgSO4, filtered and the filtrate evaporated to dryness under reduced pressure to give the title compound (0.1 g; 67%) as brownish solid. 1H-NMR (CDCl3) 1.06-1.14 (m, 3H); 1.85-1.97 (m, 2H); 4.1-4.18 (m, 2H); 7.02 (d, 1H, J=9 Hz); 8.24 (dd, 1H, J=3, 9 Hz); 8.31 (d, 1H, J=3 Hz).

Workup

  1. customThis was evaporated to dryness in vacuo
  2. customThe insoluble material was removed by filtration
  3. dry with materialThe organic phase was dried over anhydrous MgSO4
  4. filtrationfiltered
  5. customthe filtrate evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-c7faef05014d43f0ac7b56105839f3e2
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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