Hydrochloric Acid → HCID 86647490, compound

HRID 1808304Notes

Reaction equation

HRID 1808304 reaction equation
O.[OH-].[Li+].[CH3:4][O:5]/[C:6](=[CH:11]\[C:12]1[CH:17]=[CH:16][C:15]([O:18][S:19]([C:22]([F:25])([F:24])[F:23])(=[O:21])=[O:20])=[C:14]([O:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH:13]=1)/[C:7]([O:9]C)=[O:8].Cl>O1CCCC1.O>[CH2:27]([O:26][C:14]1[CH:13]=[C:12](/[CH:11]=[C:6](\[O:5][CH3:4])/[C:7]([OH:9])=[O:8])[CH:17]=[CH:16][C:15]=1[O:18][S:19]([C:22]([F:25])([F:23])[F:24])(=[O:21])=[O:20])[CH2:28][CH2:29][CH3:30]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 86647489HCID 86647489, compound

Product 1

HCID 86647490HCID 86647490, compoundYield 64.8%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
68 °C

Procedure

1.53 g (36.3 mmol) of lithium hydroxide monohydrate are added to a solution of 7.5 g (18.2 mmol) of methyl (Z)-2-methoxy-3-(3-butoxy-4-(trifluoromethanesulphonyloxy)phenyl)acrylate in 50 ml of a tetrahydrofuran/water 10/1 mixture. The reaction mixture is stirred at 68° C. for 5 hours. The reaction mixture is acidified with a 2N hydrochloric acid solution down to pH=1. The reaction mixture is extracted with two times 100 ml of a heptane/ethyl acetate 1/2 mixture. The organic phases are combined and then dried over sodium sulphate. The solvents are evaporated and then the residue is taken up in 30 ml of pentane. 4.7 g of (Z)-3-(3-Butoxy-4-(trifluoromethane-sulphonyloxy)phenyl)-2-methoxyacrylic acid are obtained in the form of a white solid.

Workup

  1. extractionThe reaction mixture is extracted with two times 100 ml of a heptane/ethyl acetate 1/2 mixture
  2. dry with materialdried over sodium sulphate
  3. customThe solvents are evaporated

Sources & evidence

ORD record
ord-85e10536929147988c04a4f94b6c6a46
Source dataset
uspto-grants-2013_01
Patent number
US08357819B2

Reaction notes

Loading…