Hydrochloric Acid → 4-[(1Z)-1-(4-Hydroxyphenyl)-2-phenylbut-1-enyl]benzaldehyde

HRID 2118213ノート

反応式

HRID 2118213 の反応式
C([O:3][CH:4](OCC)[C:5]1[CH:10]=[CH:9][C:8]([C:11]([C:22]2[CH:27]=[CH:26][C:25]([O:28]COC)=[CH:24][CH:23]=2)(O)[CH:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:13][CH3:14])=[CH:7][CH:6]=1)C.Cl>CCO>[OH:28][C:25]1[CH:26]=[CH:27][C:22](/[C:11](/[C:8]2[CH:7]=[CH:6][C:5]([CH:4]=[O:3])=[CH:10][CH:9]=2)=[C:12](\[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)/[CH2:13][CH3:14])=[CH:23][CH:24]=1

参加物

4

反応物 2

HCID 313Hydrochloric AcidHCID 693166761-[4-(Diethoxymethyl)phenyl]-1-[4-(methoxymethoxy)phenyl]-2-phenylbutan-1-ol

生成物 1

HCID 588776594-[(1Z)-1-(4-Hydroxyphenyl)-2-phenylbut-1-enyl]benzaldehyde収率 38.3%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a solution of 16 (194 g, 0.42 mol) in EtOH (1.25 L) was added 12 M HCl (250 mL). The reaction mixture was refluxed for 3 h, cooled to RT, and the volatiles were removed under reduced pressure. H2O (750 mL) was added and the mixture was extracted with ether (3×500 mL). The combined ethereal extracts were washed with H2O (750 mL), brine (750 mL), and dried over MgSO4. Concentration followed by recrystallization from hexanes afforded 52.8 g (38%) of 10 as a white solid. 1HNMR (400 MHz, DMSO-d6): δ 0.83 (t, J=7.3 Hz, 3H), 2.33 (q, J=7.3 Hz, 2H), 6.40 (d, J=8.4 Hz, 2H), 6.60 (d, J=8.4 Hz, 2H), 7.10-7.20 (m, 5H), 7.40 (d, J=7.9 Hz, 2H), 7.90 (d, J=8.1 Hz, 2H), 9.23 (s, 1H), 9.98 (s, 1H).

後処理

  1. temperatureThe reaction mixture was refluxed for 3 h
  2. customthe volatiles were removed under reduced pressure
  3. additionH2O (750 mL) was added
  4. extractionthe mixture was extracted with ether (3×500 mL)
  5. washThe combined ethereal extracts were washed with H2O (750 mL), brine (750 mL)
  6. dry with materialdried over MgSO4
  7. concentrationConcentration
  8. customfollowed by recrystallization from hexanes

出典と根拠

ORDレコード
ord-4184695a6df546fe8cc46b4748e7bbcb
出典データセット
uspto-grants-2008_10
特許番号
US07442833B2

反応ノート

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