Methanol → Methyl 4-(benzyloxy)benzoate

HRID 467237

反応式

HRID 467237 の反応式
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[H-].[Na+].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.CO>C1COCC1>[CH2:14]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

参加物

6

反応物 4

HCID 887MethanolHCID 7456MethylparabenHCID 7498Benzyl BromideHCID 24758Sodium hydride

生成物 1

HCID 299810Methyl 4-(benzyloxy)benzoate収率 24%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 75 g of methyl 4-hydroxybenzoate in 700 ml THF at 22° C. were added 19.7 g of a 60% dispersion of sodium hydride in mineral oil. After the mixture was stirred for 90 minutes, 84.3 g of benzyl bromide was added dropwise. The reaction was heated at reflux for 18 hours, cooled to room temperature and 50 ml methanol was added. The mixture was evaporated and the resulting residue extracted with three portions of ethyl acetate. The combined organic extracts were washed with water and brine, dried over magnesium sulfate and evaporated to a solid. Recrystallization from cold methanol gave 28.7 g of the title compound: 300 MHz 1H NMR (CDCl3) δ3.96 (s, 3 H), 5.19 (s, 2 H), 7.05 (d, J=9 Hz, 2 H), 7.42 (s, 5 H), 8.05 (d, J=9 Hz, 2 H).

後処理

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 18 hours
  3. customThe mixture was evaporated
  4. extractionthe resulting residue extracted with three portions of ethyl acetate
  5. washThe combined organic extracts were washed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated to a solid
  8. customRecrystallization from cold methanol

出典と根拠

ORDレコード
ord-cb4462c653234d71aa287758a817daa4
出典データセット
uspto-grants-1992_10
特許番号
US05159079

関連ノート

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