1-Bromo-4-(4-octoxyphenyl)benzene → 4-(1-Hydroxy-3-n-propylcyclopentyl)-4-n-octyloxybiphenyl

HRID 2351259Notes

Reaction equation

HRID 2351259 reaction equation
C([Li])CCC.[CH2:6]([O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][C:24](Br)=[CH:23][CH:22]=2)=[CH:17][CH:16]=1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].[CH2:28]([CH:31]1[CH2:35][CH2:34][C:33](=[O:36])[CH2:32]1)[CH2:29][CH3:30]>CCCCCC.C1(C)C=CC=CC=1.O1CCCC1>[OH:36][C:33]1([C:15]2([O:14][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:17][CH2:16]2)[CH2:34][CH2:35][CH:31]([CH2:28][CH2:29][CH3:30])[CH2:32]1

Participants

6

Reactant 3

HCID 28017871-Bromo-4-(4-octoxyphenyl)benzeneHCID 142510243-PropylcyclopentanoneHCID 178418339Butyllithium

Product 1

HCID 703921954-(1-Hydroxy-3-n-propylcyclopentyl)-4-n-octyloxybiphenyl

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 22635083Tetrahydrofuran tolueneSolvent2×

Procedure

32 ml of 15% n-butyllithium solution in hexane are added dropwise to a suspension of 18.07 g of 4-n-octyloxy-4'-bromobiphenyl in a mixture of toluene/tetrahydrofuran at -15°. After 15 minutes, a clear solution is obtained and a mixture of 6.31 g of 3-n-propylcyclopentanone and 25 ml of toluene/tetrahydrofuran is added dropwise. After the mixture has reacted for a further 16 hours at room temperature and after conventional work-up and column chromatography, 4-(1-hydroxy-3-n-propylcyclopentyl)-4-n-octyloxybiphenyl is obtained.

Workup

  1. customa clear solution is obtained
  2. additionis added dropwise
  3. customAfter the mixture has reacted for a further 16 hours at room temperature

Sources & evidence

ORD record
ord-2f1a9172bacf42948ae0c17359cce440
Source dataset
uspto-grants-1989_10
Patent number
US04873019

Reaction notes

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