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

HRID 1381590노트

반응식

HRID 1381590 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 74236Tetrabutylammonium Bromide촉매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-60bc8b2da11a46c090dcda8b7365142f
출처 데이터셋
uspto-grants-1989_02
특허 번호
US04803211

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