Hydrochloric Acid → 4-Allyl-3,5-dihydroxy-benzoic acid methyl ester

HRID 1643554노트

반응식

HRID 1643554 반응식
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([O:10]COC)[C:7]([CH2:14][CH:15]=[CH2:16])=[C:6]([O:17]COC)[CH:5]=1.Cl>CO>[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:5]=[C:6]([OH:17])[C:7]([CH2:14][CH:15]=[CH2:16])=[C:8]([OH:10])[CH:9]=1

참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 59560396Methyl 4-allyl-3,5-bis(methoxymethoxy)benzoate

생성물 1

HCID 537917924-Allyl-3,5-dihydroxy-benzoic acid methyl ester수율 79.1%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of 4-allyl-3,5-bis-methoxymethoxy-benzoic acid methyl ester (10a) (513 mg, 1.73 mmol) in MeOH (4 mL) was added 4N HCl (4 mL). The reaction mixture was stirred at room temperature overnight. The mixture was quenched with H2O (80 mL) and extracted with EtOAc (2×80 mL). The organic layers were dried over MgSO4 and concentrated to give yellow oil which was purified by flash column chromatography eluting with 15-25% EtOAc in hexanes to give a pale yellow solid (285 mg, 79% yield). 1H NMR (400 MHz, CDCl3) δ 7.20 (s, 2 H) 5.95-6.06 (m, J=5.31, 5.31 Hz, 1 H) 5.76-5.82 (m, 2 H) 5.15-5.20 (m, 1 H) 5.12-5.15 (m, 1 H) 3.90 (s, 3 H) 3.50-3.55 (m, 2 H); LCMS for C11H12O4S m/z 209.10 (M+H+).

후처리

  1. customThe mixture was quenched with H2O (80 mL)
  2. extractionextracted with EtOAc (2×80 mL)
  3. dry with materialThe organic layers were dried over MgSO4
  4. concentrationconcentrated
  5. customto give yellow oil which
  6. customwas purified by flash column chromatography
  7. washeluting with 15-25% EtOAc in hexanes

출처 및 근거

ORD 기록
ord-ffaffcbe2ce04c17a16470630eab789b
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08119624B2

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