Sodium Hydroxide → HCID 53863486, compound

HRID 343567Notes

Reaction equation

HRID 343567 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH:28]4[CH2:32][CH2:31][CH2:30][CH2:29]4)[CH:20]=3)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[CH:7][CH:6]=1)([O:3]C)=[O:2].[OH-:33].[Na+]>CO>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]#[C:12][C:13]2([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH:28]4[CH2:29][CH2:30][CH2:31][CH2:32]4)[CH:20]=3)[CH2:18][CH2:17][C:16](=[O:33])[CH2:15][CH2:14]2)=[CH:9][CH:10]=1)([OH:3])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 53973244HCID 53973244, compound

Product 1

HCID 53863486HCID 53863486, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A stirred solution of 4-(4-carbomethoxyphenylethynyl)-4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohexane (0.146 g, 0.326 mmol) in dry methanol (5 mL) was treated with 10% aqueous sodium hydroxide solution (0.46 mL, 1.15 mmol) under an argon atmosphere as described in Example 13. The crude acid was purified by chromatography (silica, ethyl acetate/methylene chloride/formic acid; 10:90:1), the product fractions washed with water three times, was stripped in vacuo, was crystalized with ether and was dried in vacuo to afford the titled compound as a white solid (0.077 g, 55%), mp 170°-171° C. Anal. (C27H28O5) calcd: C 74.98, H 6.53 found: C 74.78, H 6.54.

Workup

  1. customThe crude acid was purified by chromatography (silica, ethyl acetate/methylene chloride/formic acid; 10:90:1)
  2. washthe product fractions washed with water three times
  3. customwas crystalized with ether
  4. customwas dried in vacuo

Sources & evidence

ORD record
ord-373cd8d78de74d13b74a256a117135c3
Source dataset
uspto-grants-1999_01
Patent number
US05861421

Reaction notes

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