Lithium Hydroxide → 3'-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acid

HRID 719707Notes

Reaction equation

HRID 719707 reaction equation
O(CCSCC1C=CC(C2C=CC=C(C(O)=O)C=2)=CC=1)C1C=CC=CC=1.C([O:29][C:30]([C:32]1[CH:33]=[C:34]([C:38]2[CH:43]=[CH:42][CH:41]=[C:40]([CH2:44][S:45][CH2:46][CH2:47][O:48][C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)[CH:39]=2)[CH:35]=[CH:36][CH:37]=1)=[O:31])C.[OH-].[Li+]>C1COCC1>[O:48]([CH2:47][CH2:46][S:45][CH2:44][C:40]1[CH:39]=[C:38]([C:34]2[CH:35]=[CH:36][CH:37]=[C:32]([C:30]([OH:31])=[O:29])[CH:33]=2)[CH:43]=[CH:42][CH:41]=1)[C:49]1[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 218999924'-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acidHCID 586105963'-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acid ethyl ester

Product 1

HCID 218999913'-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acidYield 98.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3′-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acid was synthesized as described for 4′-(2-phenoxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acid. 3′-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acid ethyl ester (0.80 g, 2.04 mmol, 1 eq.) in 30% aqueous THF was treated with lithium hydroxide (0.15 g, 6.12 mmol, 3 eq.). When complete, the reaction was worked up as described leaving 3′-(2-phenoxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acid (0.73 g, 98% yield) as an orange oil that solidified on standing.

Workup

  1. custom3′-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acid was synthesized

Sources & evidence

ORD record
ord-2d3e559e87084310ab36059feaffe221
Source dataset
uspto-grants-2006_11
Patent number
US07132456B2

Reaction notes

Loading…