Benzyl Chloride → Benzyl 4-hydroxy-2-methylbenzoate

HRID 906081노트

반응식

HRID 906081 반응식
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([CH3:11])[CH:3]=1.[CH2:12](Cl)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)C(C)C)(C)C.C(=O)(O)[O-].[Na+]>>[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:7])=[C:4]([CH3:11])[CH:3]=1

참가 물질

5

반응물 4

HCID 7503Benzyl ChlorideHCID 684754-Hydroxy-o-toluic acidHCID 81531DiisopropylethylamineHCID 516892Sodium Bicarbonate

생성물 1

HCID 18006238Benzyl 4-hydroxy-2-methylbenzoate수율 79%

실험 절차

A solution of 4-hydroxy-2-methylbenzoic acid (550 mg, 3.60 mmol), benzyl chloride (458 mg, 3.60 mmol) and N,N-diisopropylethylamine (465 mg, 3.6 mmol) was stirred at 70° C. for 22 h. A solution of saturated sodium bicarbonate was added and the mixture was extracted with ethyl acetate. The organic layer was separated, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (SiO2, hexanes/ethyl acetate) to afford phenylmethyl 4-hydroxy-2-methylbenzoate (687 mg, 79%). 1H NMR (400 MHz, DMSO): 10.21-10.18 (br. s, 1H), 7.84-7.77 (d, 1H), 7.48-7.31 (m, 5H), 6.71-6.64 (br. s, 2H), 5.26 (s, 2H), 2.47 (s, 3H). MS (EI) for C15H14O3: 243 (MH+).

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (SiO2, hexanes/ethyl acetate)

출처 및 근거

ORD 기록
ord-c866fc8cb0a948ac907e1618e02799e2
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08012956B2

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