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Water → 2,12-Bis-(4-isobutylphenyl)-2,12-dimethyl-7-oxotridecanedioic acid

HRID 47987
ノート
印刷プレビュー

反応式

HRID 47987 の反応式
C([O:3][C:4](=[O:44])[C:5]([C:34]1[CH:39]=[CH:38][C:37]([CH2:40][CH:41]([CH3:43])[CH3:42])=[CH:36][CH:35]=1)([CH3:33])[CH2:6][CH2:7][CH2:8][CH2:9][C:10](=[O:32])[CH2:11][CH2:12][CH2:13][CH2:14][C:15]([C:22]1[CH:27]=[CH:26][C:25]([CH2:28][CH:29]([CH3:31])[CH3:30])=[CH:24][CH:23]=1)([CH3:21])[C:16]([O:18]CC)=[O:17])C.O.[OH-].[K+]>C(O)C>[CH2:28]([C:25]1[CH:24]=[CH:23][C:22]([C:15]([CH3:21])([CH2:14][CH2:13][CH2:12][CH2:11][C:10](=[O:32])[CH2:9][CH2:8][CH2:7][CH2:6][C:5]([C:34]2[CH:35]=[CH:36][C:37]([CH2:40][CH:41]([CH3:43])[CH3:42])=[CH:38][CH:39]=2)([CH3:33])[C:4]([OH:44])=[O:3])[C:16]([OH:18])=[O:17])=[CH:27][CH:26]=1)[CH:29]([CH3:31])[CH3:30]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 11410899Diethyl 2,12-bis(4-isobutylphenyl)-2,12-dimethyl-7-oxotridecanedioate

生成物 1

HCID 103252762,12-Bis-(4-isobutylphenyl)-2,12-dimethyl-7-oxotridecanedioic acid収率 86.2%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

2,12-Bis-(4-isobutyl-phenyl)-2,12-dimethyl-7-oxo-tridecanedioic acid diethyl ester (3.0 g, 4.95 mmol) was dissolved in ethanol (40 mL) and water (10 mL) with potassium hydroxide (4.4 g 85%). The solution was heated to reflux for six hours, cooled and concentrated. After the ethanol was removed, water (200 mL) was added and the solution was extracted with diethyl ether (100 mL). The aqueous fraction was acidified with concentrated hydrochloric acid (10 mL, to pH=1). The product was then extracted with diethyl ether (2×100 mL). The ether fractions were combined and dried with sodium sulfate (5 g). After filtration, concentration and drying under high vacuum, the reaction yielded 2,12-bis-(4-isobutyl-phenyl)-2,12-dimethyl-7-oxo-tridecanedioic acid (2.35 g, 82% yield) as a light yellow foam. 1H NMR (300 MHz, CDCl3/TMS): δ (ppm) 10.02 (bs, 2H), 7.24 (d, 4H, J=8.0 Hz), 7.09 (d, 4H, J=8.0 Hz), 2.43 (d, 4H, J=7.0 Hz), 2.33 (t, 4H, J=7.3 Hz), 2.05-1.88 (m, 2H), 1.96-1.77 (m, 4H), 1.55-1.42 (m, 10H), 1.22-1.08 (m, 4H), 0.88 (d, 12H, J=6.6). 13C NMR (75 MHz, CDCl3/TMS): δ (ppm): 211.48, 182.94, 140.43, 140.24, 129.27, 125.94, 49.71, 45.06, 42.58, 42.58, 38.91, 30.25, 24.45, 24.24, 22.58, 22.40. HRMS (LSIMS, nba): Calcd. for C35H50O5Na (MNa+): 573.3555, found: 573.3459.

後処理

  1. temperatureThe solution was heated
  2. temperatureto reflux for six hours
  3. temperaturecooled
  4. concentrationconcentrated
  5. customAfter the ethanol was removed
  6. additionwater (200 mL) was added
  7. extractionthe solution was extracted with diethyl ether (100 mL)
  8. extractionThe product was then extracted with diethyl ether (2×100 mL)
  9. dry with materialdried with sodium sulfate (5 g)
  10. filtrationAfter filtration, concentration
  11. customdrying under high vacuum

出典と根拠

ORDレコード
ord-6eabff3f43584dbd96fd1e1462fc9f9c
出典データセット
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06699910B2

反応ノート

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