Dimethyl Sulfate → 2-Methoxy-6-methyl-benzoic acid ethyl ester

HRID 8942

반응식

HRID 8942 반응식
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([OH:13])[C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9].O.[OH-].[Li+].S(OC)(O[CH3:21])(=O)=O>C1COCC1.C(OCC)C>[CH3:21][O:13][C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9]

참가 물질

6

반응물 3

HCID 6497Dimethyl SulfateHCID 168937Lithium hydroxide, monohydrateHCID 584222Ethyl 2-hydroxy-6-methylbenzoate

생성물 1

HCID 5910602-Methoxy-6-methyl-benzoic acid ethyl ester수율 91%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of ethyl 6-methylsalicylate (1.27 g, 6.97 mmol) in THF (35 mL) was added lithium hydroxide monohydrate (0.594 g, 14.2 mmol) followed by dimethyl sulfate (1.00 mL, 10.6 mmol). The resultant mixture was heated to reflux for 1 hour then cooled to room temperature. The mixture was diluted with diethyl ether (70 mL), washed with saturated aqueous NaHCO3 (4×10 mL), dried (MgSO4) and concentrated. Purification of the crude material by column chromatography on silica gel (9:1 hexanes-EtOAc) provided 1.23 g (91%) of ethyl 2-methoxy-6-methylbenzoate as a white solid. 1H NMR (CDCl3) δ 1.38 (t, 3H, J=7.2 Hz), 2.30 (s, 3H), 3.82 (s, 3H), 4.40 (q, 2H, J=7.2 Hz), 6.76 (d, 1H, J=8.4 Hz), 6.79 (d, 1H, J=7.8 Hz), 7.23 (dd, 1H, J=7.8, 8.4 Hz).

후처리

  1. temperatureto reflux for 1 hour
  2. washwashed with saturated aqueous NaHCO3 (4×10 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customPurification of the crude material by column chromatography on silica gel (9:1 hexanes-EtOAc)

출처 및 근거

ORD 기록
ord-d3bccefe8a7947608797d443fe4904be
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091217B2

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