Potassium Hydroxide → HCID 10203522, compound

HRID 873274Notes

Reaction equation

HRID 873274 reaction equation
C([O:3][C:4](=[O:36])[C:5]([CH3:35])([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH2:6][CH2:7][CH2:8][CH2:9][C:10](=[O:28])[CH2:11][CH2:12][CH2:13][CH2:14][C:15]([CH3:27])([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:16]([O:18]CC)=[O:17])C.[OH-].[K+]>C(O)C.O>[CH3:27][C:15]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)([CH2:14][CH2:13][CH2:12][CH2:11][C:10](=[O:28])[CH2:9][CH2:8][CH2:7][CH2:6][C:5]([CH3:35])([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[C:4]([OH:36])=[O:3])[C:16]([OH:18])=[O:17]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 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, 10H), 2.32 (t, 4H, J=7.2), 2.10-1.80 (m, 4H), 1.60-1.45 (m, 4H), 1.54 (s, 6H), 1.25-1.10 (m, 4H). 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 (MH4): 439.2484, found: 439.2497. HPLC: 93.7% pure.

Workup

  1. customAfter the usual workup and drying

Sources & evidence

ORD record
ord-2cb5e2d0292e45c6831c956da7e83d3e
Source dataset
uspto-grants-2015_03
Patent number
US08975300B2

Reaction notes

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