Ethanol → (6,7-Dichloro-1-oxo-2-phenyl-2-propargyl-5-indanyloxy)acetic acid

HRID 1156185Notes

Reaction equation

HRID 1156185 reaction equation
[OH-].[Na+].C(O)C.[Cl:6][C:7]1[C:15]([Cl:16])=[C:14]2[C:10]([CH2:11][C:12]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)([CH2:18][C:19]#[C:20][Si](C)(C)C)[C:13]2=[O:17])=[CH:9][C:8]=1[O:31][CH2:32][C:33]([O:35]CC)=[O:34]>O>[Cl:6][C:7]1[C:15]([Cl:16])=[C:14]2[C:10]([CH2:11][C:12]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)([CH2:18][C:19]#[CH:20])[C:13]2=[O:17])=[CH:9][C:8]=1[O:31][CH2:32][C:33]([OH:35])=[O:34]

Participants

5

Reactant 3

HCID 702Ethanol2×HCID 14798Sodium HydroxideHCID 12774091HCID 12774091, compound

Product 1

HCID 12774094(6,7-Dichloro-1-oxo-2-phenyl-2-propargyl-5-indanyloxy)acetic acidYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 50% sodium hydroxide (2.5 g.) in 50 ml. of abs. ethanol is added to a suspension of ethyl [6,7-dichloro-1-oxo-2-phenyl-2-(3-(trimethylsilyl)-2-propynyl)-5-indanyloxy]acetate (3.08 g., 6.3 mmol) in 100 ml. of abs. ethanol under an argon atmosphere. The mixture stirred at room temperature for a period of 5 hr. (excluding light) and mixed with water provides a clear yellow solution which is first extracted with ether and then acidified with dilute hydrochloric acid. The acidified solution is extracted with 1:1 ether-ethyl acetate which, after washing with brine and drying over magnesium sulfate, is concentrated under reduced pressure to afford 2.22 g. (91% yield) of (6,7-dichloro-1-oxo-2-phenyl-2-propargyl-5-indanyloxy)acetic acid as a tan solid, m.p. 238.5°-241.5° (corr.). Crystallization from isopropanol affords the indanyloxyacetic acid product as white needles, m.p. 237.5°-240° (corr.). This material is solvated with 0.17 mole of isopropanol, according to NMR analysis, and has the following elemental analysis.

Workup

  1. customprovides a clear yellow solution which
  2. extractionis first extracted with ether
  3. extractionThe acidified solution is extracted with 1:1 ether-ethyl acetate which
  4. washafter washing with brine
  5. dry with materialdrying over magnesium sulfate
  6. concentrationis concentrated under reduced pressure
  7. customto afford 2.22 g

Sources & evidence

ORD record
ord-b71f17f7ebfd479681ee1335cbb4a543
Source dataset
uspto-grants-1982_06
Patent number
US04334088

Reaction notes

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