Potassium Hydroxide → HCID 10203522, compound

HRID 239059Notes

Reaction equation

HRID 239059 reaction equation
C([C:5]1[CH:10]=[CH:9][C:8]([C:11]([CH3:40])([CH2:15][CH2:16][CH2:17][CH2:18][C:19](=[O:39])[CH2:20][CH2:21][CH2:22][CH2:23][C:24]([C:29]2[CH:34]=[CH:33][C:32](CC(C)C)=[CH:31][CH:30]=2)([CH3:28])[C:25]([OH:27])=[O:26])[C:12]([OH:14])=[O:13])=[CH:7][CH:6]=1)C(C)C.C(OC(=O)C(C)(C1C=CC=CC=1)CCCCC(=O)CCCCC(C)(C1C=CC=CC=1)C(OCC)=O)C.[OH-].[K+]>C(O)C.O>[CH3:28][C:24]([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)([CH2:23][CH2:22][CH2:21][CH2:20][C:19](=[O:39])[CH2:18][CH2:17][CH2:16][CH2:15][C:11]([CH3:40])([C:8]1[CH:7]=[CH:6][CH:5]=[CH:10][CH:9]=1)[C:12]([OH:14])=[O:13])[C:25]([OH:27])=[O:26]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 103252762,12-Bis-(4-isobutylphenyl)-2,12-dimethyl-7-oxotridecanedioic acidHCID 11329409Diethyl 2,12-dimethyl-7-oxo-2,12-diphenyltridecanedioate

Product 1

HCID 10203522HCID 10203522, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

According to the procedure given for 210f, 209d (3.93 g, 7.9 mmol) was hydrolyzed with KOH (85%, 4.0 g, 60.6 mmol) in ethanol (60 mL) and water (10 mL) at reflux for 3 h and at room temperature overnight. After the usual workup and drying, 210d (3.0 g, 87%) was obtained as an oil. 1H NMR (CDCl3): δ 7.40-7.10 (m, 10 H), 2.32 (t, 4H, J=7.2), 2.10-1.80 (m, 4 H), 1.60-1.45 (m, 4 μl), 1.54 (s, 6 H), 1.25-1.10 (m, 4 H). 13C NMR (CDCl3): δ 211.1, 182.5, 142.8, 128.4, 126.9, 126.0, 49.9, 42.3, 38.7, 24.2, 24.0, 22.3. HRMS (LSIMS, nba): Calcd for C27H35O5 (MH+): 439.2484, found: 439.2497. HPLC: 93.7% pure.

Workup

  1. customAfter the usual workup and drying

Sources & evidence

ORD record
ord-5ce4c805709440ac9d00c6ba36c83c0a
Source dataset
uspto-grants-2014_02
Patent number
US08642653B2

Reaction notes

Loading…