Ethylene Glycol → HCID 19701587、化合物

HRID 1844228ノート

反応式

HRID 1844228 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=[O:6].[OH:11][CH2:12][CH2:13]O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]2[O:11][CH2:12][CH2:13][O:6]2)[CH:7]=[CH:8][C:9]=1[OH:10]

参加物

5

反応物 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 763083-Bromo-4-hydroxybenzaldehyde

生成物 1

HCID 19701587HCID 19701587、化合物収率 95%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

3-Bromo-4-hydroxybenzaldehyde (2a, 10.0 g, 49.8 mmol) was heated at reflux with 1,2-dihydroxyethane (25 g, 0.4 mol) in toluene (150 mL) in the presence of p-toluenesulfonic acid (950 mg) for 48 h in an apparatus fitted with a Dean-Stark trap. The reaction mixture was concentrated by reduced pressure evaporation, washed with aqueous sodium hydrogen carbonate, water, brine, dried over Na2SO4, evaporated to dryness and then passed through a short silica gel column using a hexanes-ethyl acetate mixture (5:1) with a few drops of triethylamine as eluent to afford the protected product 3a (11.0 g, 95%) as a crystalline solid. Rf=0.38 (25% EtOAc-hexanes): mp 76-78° C. IR (neat) 3351, 2954, 2891, 1608, 1499, 1431, 1284, 1100 cm−1; 1H NMR (300 MHz, CDCl3) δ 7.57 (d, J=1.8 Hz, 1H), 7.28 (dd, J=8.4, 2.4 Hz, 1H), 6.96 (d, J=8.7 Hz, 1H), 5.69 (s, 1H), 4.03 (m, 4H); 13C NMR (75 MHz, CDCl3) δ 152.9, 131.5, 130.2, 127.5, 115.8, 110.0, 102.7, 65.2; CIMS (m/z, rel intensity) 247 (MH++2, 7), 245 (MH+, 7), 203 (100), 201 (100), 175 (4), 173(5), 94 (1).

後処理

  1. customfitted with a Dean-Stark trap
  2. concentrationThe reaction mixture was concentrated by reduced pressure evaporation
  3. washwashed with aqueous sodium hydrogen carbonate, water, brine
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness

出典と根拠

ORDレコード
ord-b63c841473d441b280d7a82029c69b0c
出典データセット
uspto-grants-2015_02
特許番号
US08946287B2

反応ノート

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