Potassium Hydroxide → HCID 13384234, compound

HRID 2419915Notes

Reaction equation

[Cl:1][C:2]1[CH:22]=[CH:21][C:5](OC(C(F)(F)F)(C(F)(F)F)C(OCC)=O)=[CH:4][CH:3]=1.[F:23][C:24]1[CH:44]=[CH:43][C:27]([O:28][C:29]([C:39]([F:42])([F:41])[F:40])([C:35]([F:38])([F:37])[F:36])[C:30]([O:32]CC)=[O:31])=[CH:26][CH:25]=1.[C:45]1([O:55][C:56]([C:66]([F:69])([F:68])[F:67])([C:62]([F:65])([F:64])[F:63])[C:57]([O:59]CC)=[O:58])[C:54]2[C:49](=[CH:50][CH:51]=[CH:52][CH:53]=2)[CH:48]=[CH:47][CH:46]=1.[C:70]1([C:91]2[CH:96]=[CH:95][CH:94]=[CH:93][CH:92]=2)[CH:75]=[CH:74][C:73]([O:76][C:77]([C:87]([F:90])([F:89])[F:88])([C:83]([F:86])([F:85])[F:84])[C:78]([O:80]CC)=[O:79])=[CH:72][CH:71]=1.ClC1C=CC([C:104]2[CH:124]=[CH:123][C:107]([O:108][C:109]([C:119]([F:122])([F:121])[F:120])([C:115]([F:118])([F:117])[F:116])[C:110]([O:112]CC)=[O:111])=[CH:106][CH:105]=2)=CC=1.[OH-].[K+]>>[F:23][C:24]1[CH:25]=[CH:26][C:27]([O:28][C:29]([C:35]([F:36])([F:37])[F:38])([C:39]([F:42])([F:41])[F:40])[C:30]([OH:32])=[O:31])=[CH:43][CH:44]=1.[C:45]1([O:55][C:56]([C:62]([F:63])([F:64])[F:65])([C:66]([F:67])([F:69])[F:68])[C:57]([OH:59])=[O:58])[C:54]2[C:49](=[CH:50][CH:51]=[CH:52][CH:53]=2)[CH:48]=[CH:47][CH:46]=1.[C:70]1([C:91]2[CH:96]=[CH:95][CH:94]=[CH:93][CH:92]=2)[CH:71]=[CH:72][C:73]([O:76][C:77]([C:83]([F:84])([F:85])[F:86])([C:87]([F:89])([F:90])[F:88])[C:78]([OH:80])=[O:79])=[CH:74][CH:75]=1.[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([C:104]2[CH:124]=[CH:123][C:107]([O:108][C:109]([C:119]([F:120])([F:122])[F:121])([C:115]([F:118])([F:116])[F:117])[C:110]([OH:112])=[O:111])=[CH:106][CH:105]=2)=[CH:4][CH:3]=1

Participants

Reactant 6

HCID 14797Potassium Hydroxide2×

HCID 13384231HCID 13384231, compound

HCID 13384233HCID 13384233, compound

HCID 13384235HCID 13384235, compound

HCID 13384237HCID 13384237, compound

HCID 13384239HCID 13384239, compound2×

Product 4

HCID 13384234HCID 13384234, compound

HCID 13384236HCID 13384236, compound

HCID 13384238HCID 13384238, compound

HCID 13384240HCID 13384240, compound

Procedure

The above process is repeated except that the ethyl 2-(4-chlorophenoxy)-3,3,3-trifluoro-2-trifluoromethylpropionate is replaced by ethyl 2-(4-fluorophenoxy)-3,3,3-trifluoro-2-trifluoromethylpropionate (8.6 g.), ethyl 2-(1-naphthyloxy)-3,3,3-trifluoro-2-trifluoromethylpropionate (4.8 g.), ethyl 2-(4-biphenylyloxy)-3,3,3-trifluoro-2-trifluoromethylpropionate (1.96 g.) or ethyl 2-[4-(4-chlorophenyl)phenoxy]-3,3,3-trifluoro-2-trifluoromethylpropionate (3.35 g.) and the 19.2 ml. of 4.5N-aqueous potassium hydroxide is replaced by an equivalent quantity (based on the amount of starting ester) of 5.2N-aqueous potassium hydroxide. In the case of ethyl 2-(1-naphthyloxy)-3,3,3-trifluoro-2-trifluoromethylpropionate, the hydrolysis is continued for 41/2 hours. In each case the sublimation step is omitted, and the residue after evaporation of the ethereal extract is crystallised from light petroleum (b.p. 60°-80° C.) to give 2-(4-fluorophenoxy)-3,3,3-trifluoro-2-trifluoromethylpropionic acid, m.p. 77°-78° C. (1.5 g.), 2-(1-naphthyloxy)-3,3,3-trifluoro-2-trifluoromethylpropionic acid, m.p. 125°-126° C. (0.46 g.), 2-(4-biphenylyloxy)-3,3,3-trifluoro-2-trifluoromethylpropionic acid, m.p. 137°-138° C. (1.15 g.), or 2-[4-(4-chlorophenyl)phenoxy]-3,3,3-trifluoro-2-trifluoromethylpropionic acid, m.p. 159°-160° C. (1.15 g.), respectively.

Workup

custom2 hours
customthe residue after evaporation of the ethereal
extractionextract
customis crystallised from light petroleum (b.p. 60°-80° C.)

Sources & evidence

ORD record: ord-495f6699929341ffaabc2a9cba180dc2
Source dataset: uspto-grants-1978_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04107329

Reaction notes

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