Sodium Cyanide → 3-Cyano-4-hydroxybenzoic acid

HRID 710404ノート

反応式

HRID 710404 の反応式
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]

参加物

5

反応物 3

HCID 8929Sodium CyanideHCID 448288973-Iodo-4-propoxybenzoic acidHCID 178418546HCID 178418546、化合物

生成物 1

HCID 111374633-Cyano-4-hydroxybenzoic acid収率 85.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
110 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-c7faef05014d43f0ac7b56105839f3e2
出典データセット
uspto-grants-2015_11
特許番号
US09181182B2

反応ノート

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