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

HRID 47987Notes

Reaction equation

HRID 47987 reaction equation
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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-6eabff3f43584dbd96fd1e1462fc9f9c
Source dataset
uspto-grants-2004_03
Patent number
US06699910B2

Reaction notes

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