Hydroxyphenylacetic acid → Benzyl 2-(4-hydroxyphenyl)acetate

HRID 2224

반응식

HRID 2224 반응식
[H-].[Na+].CCCCCC.[OH:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C:17]([OH:19])=[O:18])=[CH:12][CH:11]=1.[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CN(C=O)C>[OH:9][C:10]1[CH:11]=[CH:12][C:13]([CH2:16][C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])=[CH:14][CH:15]=1

참가 물질

6

반응물 4

HCID 127Hydroxyphenylacetic acidHCID 7498Benzyl BromideHCID 8058HexaneHCID 24758Sodium hydride

생성물 1

HCID 11107524Benzyl 2-(4-hydroxyphenyl)acetate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
4 °C

실험 절차

Sodium hydride (50% w/w dispersion in mineral oil, 3.7 g) was treated under argon with repeated washes of hexane. The oil-free residue was suspended in dry DMF (100 ml) and 4-hydroxyphenylacetic acid (13.0 g) was added portionwise to the stirred cooled (4° C.) mixture. After 30 minutes, benzyl bromide (9.2 ml) was added dropwise and, after a further 1 hour at 4° C., stirring was continued overnight at ambient temperature. The solvent was evaporated in vacuo and the residue partitioned between ethyl acetate and water. The aqueous phase was re-extracted with further ethyl acetate and the combined organic extracts washed with water and brine, then dried (MgSO4) and evaporated. The crystalline residue gave benzyl 4-hydroxyphenylacetate, 17.8 g, as off-white crystals: m.p. 70°-72° C.; NMR (CDCl3) δ 7.32(5H, m), 7.14(2H, d), 6.76(2H, d), 5.12(2H, s), 3.59(2H, s); m/e 242 (M.)+.

후처리

  1. waitwas continued overnight at ambient temperature
  2. customThe solvent was evaporated in vacuo
  3. customthe residue partitioned between ethyl acetate and water
  4. extractionThe aqueous phase was re-extracted with further ethyl acetate
  5. washthe combined organic extracts washed with water and brine
  6. dry with materialdried (MgSO4)
  7. customevaporated

출처 및 근거

ORD 기록
ord-a4c192010f8d498c9feb99faee7fc4d5
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05728701

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