Sodium Hydroxide → (2-Benzyloxy-5-chloro-[1,1':2'1'']terphenyl-3''-yl)-acetic acid

HRID 269525Notes

Reaction equation

HRID 269525 reaction equation
C([O:3][C:4](=[O:33])[CH2:5][C:6]1[CH:7]=[C:8]([C:12]2[C:13]([C:18]3[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:19]=3[O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:9]=[CH:10][CH:11]=1)C.[OH-].[Na+]>C(O)C.O.C(OCC)C.CCCC(C)C>[CH2:26]([O:25][C:19]1[CH:20]=[CH:21][C:22]([Cl:24])=[CH:23][C:18]=1[C:13]1[C:12]([C:8]2[CH:9]=[CH:10][CH:11]=[C:6]([CH2:5][C:4]([OH:33])=[O:3])[CH:7]=2)=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 58730996(2-Benzyloxy-5-chloro-[1,1';2',1'']terphenyl-3''-yl)-acetic acid ethyl ester

Product 1

HCID 10320411(2-Benzyloxy-5-chloro-[1,1':2'1'']terphenyl-3''-yl)-acetic acidYield 80.2%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 21882825Ether isohexaneSolvent

Procedure

A solution of (2-benzyloxy-5-chloro-[1,1′;2′,1″]terphenyl-3″-yl)-acetic acid ethyl ester (112 mg, 0.25 mmol) in ethanol (5 ml) and 2M sodium hydroxide (1 ml, 2 mmol) was stirred at room temperature for 1 hour then diluted with water and 1:1 diethyl ether/iso-hexane. The aqueous suspension was separated, acidified with 1M hydrochloric acid and extracted with diethyl ether. The organic solution was dried (MgSO4) evaporated to dryness and the residue triturated with iso-hexane to give the title compound as a white solid (86 mg, 80%).

Workup

  1. customThe aqueous suspension was separated
  2. extractionextracted with diethyl ether
  3. dry with materialThe organic solution was dried (MgSO4)
  4. customevaporated to dryness
  5. customthe residue triturated with iso-hexane

Sources & evidence

ORD record
ord-c2d6a381c9c743618144f624046ec560
Source dataset
uspto-grants-2008_11
Patent number
US07446222B2

Reaction notes

Loading…