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

HRID 1459433ノート

反応式

HRID 1459433 の反応式
[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

参加物

5

反応物 3

HCID 1254-Hydroxybenzyl AlcoholHCID 7748Ethyl bromoacetateHCID 10796Cesium carbonate

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-1ea32c3b8aeb45d982843e20f0767ee5
出典データセット
uspto-grants-1998_12
特許番号
US05854245

反応ノート

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