Sodium Hydroxide → HCID 19004275, compound

HRID 2225704Notes

Reaction equation

HRID 2225704 reaction equation
C[O:2][C:3](=[O:26])[C:4](=[O:25])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][O:14][C:15]23[CH2:24][CH:19]4[CH2:20][CH:21]([CH2:23][CH:17]([CH2:18]4)[CH2:16]2)[CH2:22]3)=[CH:7][CH:6]=1.[OH-].[Na+]>CO>[O:25]=[C:4]([C:5]1[CH:6]=[CH:7][C:8]([O:11][CH2:12][CH2:13][O:14][C:15]23[CH2:24][CH:19]4[CH2:18][CH:17]([CH2:23][CH:21]([CH2:20]4)[CH2:22]2)[CH2:16]3)=[CH:9][CH:10]=1)[C:3]([OH:26])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54193808HCID 54193808, compound

Product 1

HCID 19004275HCID 19004275, compoundYield 79.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of alpha-oxo-4-[[2-[tricyclo(3.3.1.1-3,7)dec-1-yloxy]ethyl]oxy]benzeneacetic acid methyl ester (0.685 g) in methanol (10 mL) heated on the steam bath and added sufficient actone to dissolve the solids. Then 0.5N sodium hydroxide (8 mL) was added and the mixture was treated as in Example 19. Extraction with dichloromethane provided material which was crystallized from diethyl ether-hexane to give 0.524 g of colorless alpha-oxo-4-[[2-[tricyclo(3.3.1.1-3,7)dec-1-yloxy]ethyl]oxy]benzeneacetic acid, mp 155°-156° C.

Workup

  1. temperatureheated on the steam bath
  2. additionadded sufficient actone
  3. dissolutionto dissolve the solids
  4. additionthe mixture was treated as in Example 19
  5. extractionExtraction with dichloromethane provided material which
  6. customwas crystallized from diethyl ether-hexane

Sources & evidence

ORD record
ord-c8b1b1e7b3d34e48b4339311b2c4c8fa
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

Loading…