4-Hydroxybenzyl Alcohol → Acetic acid, [4-(hydroxymethyl)phenoxy]-, ethyl ester

HRID 1381590ノート

反応式

HRID 1381590 の反応式
[CH:1]1[C:6]([CH2:7][OH:8])=[CH:5][CH:4]=[C:3]([OH:9])[CH:2]=1.Br[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>[OH:8][CH2:7][C:6]1[CH:5]=[CH:4][C:3]([O:9][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:2][CH:1]=1

参加物

7

反応物 4

HCID 1254-Hydroxybenzyl AlcoholHCID 6228DimethylformamideHCID 7748Ethyl bromoacetateHCID 11430Potassium Carbonate

生成物 1

HCID 11413157Acetic acid, [4-(hydroxymethyl)phenoxy]-, ethyl ester収率 63.8%

試薬・触媒・溶媒 2

HCID 74236Tetrabutylammonium Bromide触媒HCID 8857Ethyl Acetate溶媒

実験手順

To a mixture of 2.00 g of p-hydroxybenzyl alcohol, 3.23 g of ethyl bromoacetate, 2.45 g of anhydrous potassium carbonate and 15 ml of N,N-dimethylformamide was added tetra-n-butylammonium bromide in a catalytic amount. The mixture was stirred at room temperature for 3 hours. The reaction mixture was diluted with ethyl acetate and insoluble matters were filtered off. The filtrate was washed with an aqueous sodium hydroxide solution and water, in this sequence. After drying over anhydrous magnesium sulfate, the solvent was distilled off. The residue was applied to silica gel column chromatography. Elution with a solvent mixture of hexane-ethyl acetate (3:2) gave 2.16 g of oily ethyl [p-(hydroxymethyl)phenoxy]acetate.

後処理

  1. filtrationwere filtered off
  2. washThe filtrate was washed with an aqueous sodium hydroxide solution and water, in this sequence
  3. dry with materialAfter drying over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off
  5. washElution
  6. additionwith a solvent mixture of hexane-ethyl acetate (3:2)

出典と根拠

ORDレコード
ord-60bc8b2da11a46c090dcda8b7365142f
出典データセット
uspto-grants-1989_02
特許番号
US04803211

反応ノート

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