Hydrochloric Acid → 4-Methoxyresorcinol

HRID 2272775

반응식

HRID 2272775 반응식
C(OC[O:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH:13](C)C)=[C:8]([O:16]COCC)[C:7]=1C)C.Cl.O>CO>[CH3:13][O:12][C:9]1[CH:10]=[CH:11][C:6]([OH:5])=[CH:7][C:8]=1[OH:16]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 251402561,3-Bis(ethoxymethoxy)-4-isopropoxy-2-methylbenzene

생성물 1

HCID 30839364-Methoxyresorcinol수율 127.9%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A solution of 5c (157 mg, 0.53 mmol) in MeOH (4.40 mL) at room temperature was treated dropwise with 3 M HCl (1.40 mL, 4.21 mmol), then heated to reflux for one hour. Water (5 mL) was added and the solution was extracted with EtOAc (3×10 mL). Combined organic fractions were washed with saturated aqueous NaCl, dried (Na2SO4), filtered, and concentrated to afford 6c as a red amorphous solid (95 mg, 99%): 1H NMR (CDCl3, 500 MHz) δ 6.54 (d, J=8.7 Hz, 1H), 6.21 (d, J=8.7 Hz, 1H), 5.78 (s, 1H), 4.37-4.32 (m, 1H), 2.09 (s, 3H), 1.25 (d, J=6.1 Hz, 6H); 13C NMR (CDCl3, 125 MHz) δ 147.7, 144.9, 137.5, 110.8, 109.8, 104.0, 71.7, 21.3 (2C); IR (film) νmax 3526, 2974, 2924, 2853, 1717, 1607, 1475, 1238, 1113, 1067, 928, 887, 791 cm−1.

후처리

  1. temperatureheated
  2. temperatureto reflux for one hour
  3. extractionthe solution was extracted with EtOAc (3×10 mL)
  4. washCombined organic fractions were washed with saturated aqueous NaCl
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-fba566e5f84b4421965d484a4426aaee
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09120774B2

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