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

HRID 1078025Notes

Reaction equation

HRID 1078025 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][CH2:22][CH3:23])=[C:11]([F:24])[CH:10]=2)[CH:5]=[CH:6][C:7]=1[OH:8].[CH2:25]([CH:27]1[CH2:30][CH:29]([C:31](Cl)=[O:32])[CH2:28]1)[CH3:26].C(C1CC(C(Cl)=O)C1)CCCCCCC>>[CH2:25]([CH:27]1[CH2:30][CH:29]([C:31]([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][CH2:22][CH3:23])=[C:11]([F:24])[CH:10]=3)=[CH:3][C:2]=2[F:1])=[O:32])[CH2:28]1)[CH3:26]

Participants

4

Reactant 3

HCID 147941713,3'-Difluoro-4-hydroxy-4'-octyloxybiphenylHCID 450812713-Ethylcyclobutanecarboxylic acid chlorideHCID 537428853-Octylcyclobutanecarboxylic acid chloride

Product 1

HCID 194309483,3'-Difluoro-4-octyloxybiphenyl-4'-yl 3-ethylcyclobutanecarboxylateYield 70.2%

Procedure

Except that 0.60 g of 3,3'-difluoro-4-hydroxy-4'-octyloxybiphenyl obtained in Example 5-(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=4/1), the operation was performed in the same manner as in Example 9-(g) to obtain 0.56 g (yield 30.9%) of 3,3'-difluoro-4-octyloxybiphenyl-4'-yl 3-ethylcyclobutanecarboxylate.

Workup

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

Sources & evidence

ORD record
ord-b2372939df6f40ae94004eefb6b77b66
Source dataset
uspto-grants-1996_08
Patent number
US05545747

Reaction notes

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