5-(Benzyloxy)-2-hydroxybenzaldehyde → 4-Benzyloxy-2-(hydroxy-phenyl-methyl)-phenol

HRID 398168노트

반응식

HRID 398168 반응식
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([OH:17])=[C:13]([CH:16]=1)[CH:14]=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18]1([Li])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([OH:17])=[C:13]([CH:14]([OH:15])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:16]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

4

반응물 2

HCID 8783625-(Benzyloxy)-2-hydroxybenzaldehydeHCID 178506676HCID 178506676, 화합물

생성물 1

HCID 222611734-Benzyloxy-2-(hydroxy-phenyl-methyl)-phenol수율 93%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of phenol (Kappe, T.; Witoszynskyj, T. Arch. Pharm. (1975), 308 (5), 339-346) (1.14 g, 5.00 mmol) in THF (15 mL) was cooled in a dry ice/acetone bath and treated dropwise with phenyllithium (7.5 mL, 13.5 mmol, 1.8M in cyclohexane/ethyl ether 70/30). The reaction mixture was allowed to warm gradually to ambient temperature. After 18 h, the reaction was quenched with aqueous saturated NH4Cl solution (1 mL) and partitioned between ethyl acetate (50 mL) and 1N HCl (20 mL). The organic layer was washed with brine (75 mL), dried (Na2SO4), and concentrated to a brown oil (2.3 g). The crude product was purified by flash chromatography using hexanes:ethyl acetate (3:1 to 2:1) to give a pale yellow oil (1.42 g, 93%): 1H NMR (400 MHz, CDCl3) δ2.79 (s, 1H), 4.92 (s, 2H), 5.95, (s, 1H), 6.51 (s, 1H), 6.81 (d, 3H, J=1.5 Hz), 7.28-7.38 (s, 10H); MS (ES) m/e 305 [M−1].

후처리

  1. customthe reaction was quenched with aqueous saturated NH4Cl solution (1 mL)
  2. custompartitioned between ethyl acetate (50 mL) and 1N HCl (20 mL)
  3. washThe organic layer was washed with brine (75 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated to a brown oil (2.3 g)
  6. customThe crude product was purified by flash chromatography

출처 및 근거

ORD 기록
ord-ede1f8734837448495428e80c2d4686a
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06610696B2

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