3,3'-Difluoro-4-hydroxy-4'-heptyloxybiphenyl → 3,3'-Difluoro-4-heptyloxybiphenyl-4'-yl 3-ethylcyclobutanecarboxylate

HRID 1078026Notes

Reaction equation

HRID 1078026 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[C:11]([F:23])[CH:10]=2)[CH:5]=[CH:6][C:7]=1[OH:8].[CH2:24]([CH:26]1[CH2:29][CH:28]([C:30](Cl)=[O:31])[CH2:27]1)[CH3:25].C(C1CC(C(Cl)=O)C1)CCCCCCC>>[CH2:24]([CH:26]1[CH2:29][CH:28]([C:30]([O:8][C:7]2[CH:6]=[CH:5][C:4]([C:9]3[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[C:11]([F:23])[CH:10]=3)=[CH:3][C:2]=2[F:1])=[O:31])[CH2:27]1)[CH3:25]

Participants

4

Reactant 3

HCID 194309383,3'-Difluoro-4-hydroxy-4'-heptyloxybiphenylHCID 450812713-Ethylcyclobutanecarboxylic acid chlorideHCID 537428853-Octylcyclobutanecarboxylic acid chloride

Product 1

HCID 194309363,3'-Difluoro-4-heptyloxybiphenyl-4'-yl 3-ethylcyclobutanecarboxylateYield 91.8%

Procedure

Except that 0.60 g of the crude 3,3'-difluoro-4-hydroxy-4'-heptyloxybiphenyl obtained in Example 6-(c) was used in place of 0.7 g of the crude 3,3'-difluoro-4-hydroxy-4'-decyloxybiphenyl and 0.3 g of 3-ethylcyclobutanecarboxylic acid chloride obtained in Example 13-(d) in place of 0.5 g of the 3-octylcyclobutanecarboxylic acid chloride used in Example 9-(g) and purification was carried out by way of column chromatography on silica gel (eluent: hexane/benzene=2/1), the operation was performed in the same manner as in Example 9-(g) to obtain 0.74 g (yield 90.6%) of 3,3'-difluoro-4-heptyloxybiphenyl-4'-yl 3-ethylcyclobutanecarboxylate.

Workup

  1. customused in Example 9-(g) and purification

Sources & evidence

ORD record
ord-9b1446721f3d484d9216b711b18ec5b7
Source dataset
uspto-grants-1996_08
Patent number
US05545747

Reaction notes

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