Hydrochloric Acid → HCID 14350673, compound

HRID 2291539Notes

Reaction equation

HRID 2291539 reaction equation
C([O:4][CH:5]1[C@@:17]2([CH2:18][CH2:19][CH3:20])[C:12](=[CH:13][C:14](=[O:21])[CH2:15][CH2:16]2)[C:11]2[C:6]1=[CH:7][C:8]([O:24][CH2:25][C:26]([O:28]CC)=[O:27])=[C:9]([Cl:23])[C:10]=2[Cl:22])(=O)C.CO.[OH-].[Na+].Cl>O>[Cl:22][C:10]1[C:9]([Cl:23])=[C:8]([O:24][CH2:25][C:26]([OH:28])=[O:27])[CH:7]=[C:6]2[C:11]=1[C:12]1[C@:17]([CH2:18][CH2:19][CH3:20])([CH:5]2[OH:4])[CH2:16][CH2:15][C:14](=[O:21])[CH:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 14350675HCID 14350675, compound

Product 1

HCID 14350673HCID 14350673, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of ethyl [(9-acetoxy-5,6-dichloro-3-oxo-9a(R)-propyl-2,3,9,9a-tetrahydro-1H-fluoren-7-yl)oxy]acetate (4.27 g, 0.0094 mol), methanol (75 ml) and 1N sodium hydroxide (21 ml) was stirred at 25° C. for 4 hours, diluted with water (250 ml), acidified with HCl and extracted with ether and methylene chloride. The combined organic extracts were combined, washed with H2O, dried over MgSO4 and evaporated in vacuo to give [(5,6-dichloro-9-hydroxy-3-oxo-9a(R)-propyl-2,3,9,9a-tetrahydro-1H-fluoren-7-yl)oxy]acetic acid which melted at 206°-208° C.

Workup

  1. extractionextracted with ether and methylene chloride
  2. washwashed with H2O
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-942af89c453b482ebd1e6cdb44c23634
Source dataset
uspto-grants-1989_01
Patent number
US04797391

Reaction notes

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