(+/-)-Methyl 2-(2-naphthylmethoxy)-3,3,3-trifluoro-2-methylpropionate → (+/-)-2-(2-Naphthylmethoxy)-3,3,3-trifluoro-2-methylpropionic acid

HRID 2419907Notes

Reaction equation

HRID 2419907 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([CH2:12][O:13][C:14]([CH3:23])([C:19]([F:22])([F:21])[F:20])[C:15]([O:17]C)=[O:16])[CH:6]=[CH:5]2.[CH:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[CH:26][C:25]=1[CH2:34][O:35][C:36]([CH3:45])([C:41]([F:44])([F:43])[F:42])[C:37]([O:39]C)=[O:38].[C:46]1([CH2:56][O:57][C:58]([CH3:67])([C:63]([F:66])([F:65])[F:64])[C:59]([O:61]C)=[O:60])[C:55]2[C:50](=[CH:51][CH:52]=[CH:53][CH:54]=2)[CH:49]=[CH:48][CH:47]=1.C1(C)C=CC=CC=1.C1CCCCC1>C1CCCCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([CH2:12][O:13][C:14]([CH3:23])([C:19]([F:20])([F:21])[F:22])[C:15]([OH:17])=[O:16])[CH:6]=[CH:5]2.[CH:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[CH:26][C:25]=1[CH2:34][O:35][C:36]([CH3:45])([C:41]([F:42])([F:43])[F:44])[C:37]([OH:39])=[O:38].[C:46]1([CH2:56][O:57][C:58]([CH3:67])([C:63]([F:64])([F:65])[F:66])[C:59]([OH:61])=[O:60])[C:55]2[C:50](=[CH:51][CH:52]=[CH:53][CH:54]=2)[CH:49]=[CH:48][CH:47]=1

Participants

8

Reactant 4

HCID 13384286(+/-)-Methyl 2-(2-naphthylmethoxy)-3,3,3-trifluoro-2-methylpropionateHCID 13384288(+/-)-Methyl 2-(6-chloro-2-naphthylmethoxy)-3,3,3-trifluoro-2-methylpropionateHCID 13384292(+/-)-Methyl 2-(1-naphthylmethoxy)-3,3,3-trifluoro-2-methylpropionateHCID 21910790Toluene cyclohexane

Product 3

HCID 13384287(+/-)-2-(2-Naphthylmethoxy)-3,3,3-trifluoro-2-methylpropionic acidHCID 13384289(+/-)-2-(6-Chloro-2-naphthylmethoxy)-3,3,3-trifluoro-2-methylpropionic acidHCID 13384293(+/-)-2-(1-Naphthylmethoxy)-3,3,3-trifluoro-2-methylpropionic acid

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

The above process is repeated with (±)-methyl 2-(6-chloro-2-naphthylmethoxy)-3,3,3-trifluoro-2-methylpropionate, (±)-methyl 2-(2-naphthylmethoxy)-3,3,3-trifluoro-2-methyl-propionate or (±)-methyl 2-(1-naphthylmethoxy)-3,3,3-trifluoro-2-methylpropionate except that the reaction is carried out for 41/2, 2 and 21/2 hours respectively to give (±)-2-(6-chloro-2-naphthylmethoxy)-3,3,3-trifluoro-2-methylpropionic acid, m.p. 150°-153° C. (from toluene-cyclohexane), (±)-2-(2-naphthylmethoxy)-3,3,3-trifluoro-2-methylpropionic acid, m.p. 116°-118° C. (from cyclohexane) or (±)-2-(1-naphthylmethoxy)-3,3,3-trifluoro-2-methylpropionic acid, m.p. 82°-84° C. (from light petroleum b.p. 60°-80° C.) respectively.

Workup

  1. custom2 hours

Sources & evidence

ORD record
ord-2fbf3c2983a3473d84740d4c243ab2ff
Source dataset
uspto-grants-1978_08
Patent number
US04107329

Reaction notes

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