Dimethylformamide → 3-Ethyl-4-hydroxy-5-methyl-benzoic acid benzyl ester

HRID 2065904ノート

反応式

HRID 2065904 の反応式
[CH2:1]([C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([CH3:13])[C:11]=1[OH:12])[C:6]([OH:8])=[O:7])[CH3:2].CN(C=O)C.[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>O>[CH2:19]([O:7][C:6](=[O:8])[C:5]1[CH:9]=[C:10]([CH3:13])[C:11]([OH:12])=[C:3]([CH2:1][CH3:2])[CH:4]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 592347773-Ethyl-4-hydroxy-5-methyl-benzoic acid

生成物 1

HCID 685502593-Ethyl-4-hydroxy-5-methyl-benzoic acid benzyl ester収率 90%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
50 °C

実験手順

To a solution of 3-ethyl-4-hydroxy-5-methyl-benzoic acid (80.3 g, 0.446 mol) is DMF (500 mL), KHCO3 (53.5 g, 0.535 mol) followed by benzylbromide (114.3 g, 0.668 mol) is added. The mixture is stirred at 50° C. for 18 h before it is cooled to rt, diluted with water (250 mL), and extracted with TBME (2×250 mL). The org. extracts are washed with water, and then concentrated. The crude product is purified by CC on silica gel eluting with heptane:EA 19:1 to 9:1 to give 3-ethyl-4-hydroxy-5-methyl-benzoic acid benzyl ester (108.5 g) as a beige solid; 1H NMR (CDCl3): δ1.28 (t, J=7.5 Hz, 3H), 2.30 (s, 3H), 2.68 (q, J=7.8 Hz, 2H), 5.24 (s, 1H), 5.37 (s, 2H), 7.33-7.45 (m, 3H), 7.45-7.50 (m, 2H), 7.77 (s, 1H), 7.79 (s, 1H).

後処理

  1. additionis added
  2. temperatureis cooled to rt
  3. extractionextracted with TBME (2×250 mL)
  4. washextracts are washed with water
  5. concentrationconcentrated
  6. customThe crude product is purified by CC on silica gel eluting with heptane:EA 19:1 to 9:1

出典と根拠

ORDレコード
ord-875d30a2390d468f9b250e313a3b1ac7
出典データセット
uspto-grants-2012_10
特許番号
US08288554B2

反応ノート

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