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

HRID 1459433노트

반응식

HRID 1459433 반응식
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19]>CN(C=O)C>[OH:7][CH2:6][C:5]1[CH:8]=[CH:9][C:2]([O:1][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:3][CH:4]=1

참가 물질

5

반응물 3

HCID 1254-Hydroxybenzyl AlcoholHCID 7748Ethyl bromoacetateHCID 10796Cesium carbonate

생성물 1

HCID 11413157Acetic acid, [4-(hydroxymethyl)phenoxy]-, ethyl ester수율 59%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a 500 mL round bottomed flask with a stirring bar and an argon inlet was added 4-hydroxybenzyl alcohol (7.50 g, 60.42 mmol), Cs2CO3 (29.53 g, 90.63 mmol), DMF (100 mL), and ethyl bromoacetate (11.09 g, 66.46 mmol). This mixture was stirred at ambient temperature for 2 h. The mixture was filtered and the filtrate was concentrated in vacuo. The residue was partitioned between EtOAc and water. The layers were separated and the organic phase was washed with two additional portions of water. Drying (MgSO4), filtration and removal of the solvent in vacuo, gave an oil. This material was chromatographed on 250 g of silica gel using 1:1 EtOAc-hexane as eluant. There was obtained ethyl 2-(4-hydroxymethyl-phenoxy)acetate 35-4 (7.47 g, 59%) as an oil. 1H NMR (CDCl3): δ 1.29 (t, J=7 Hz, 3H), 2.07 (br s, 1H), 4.26 (q, J=7 Hz, 2H), 4.58 (s, 2H), 4.60 (s, 2H), 6.88 (d, J=9 Hz, 2H), 7.27 (d, J=9 Hz, 2H).

후처리

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was partitioned between EtOAc and water
  4. customThe layers were separated
  5. washthe organic phase was washed with two additional portions of water
  6. customDrying
  7. filtration(MgSO4), filtration and removal of the solvent in vacuo
  8. customgave an oil
  9. customThis material was chromatographed on 250 g of silica gel using 1:1 EtOAc-hexane as eluant

출처 및 근거

ORD 기록
ord-1ea32c3b8aeb45d982843e20f0767ee5
출처 데이터셋
uspto-grants-1998_12
특허 번호
US05854245

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