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Sodium hydride → HCID 19818264, compound

HRID 1086764
Notes
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Reaction equation

HRID 1086764 reaction equation
[CH2:1]([O:5][C:6]([O:8][CH:9]([CH3:19])[CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)=[O:7])[CH2:2][CH2:3][CH3:4].[H-].[Na+].[CH2:22]([C:30]1[CH:35]=[CH:34][C:33]([C:36]2[CH:41]=[CH:40][C:39]([CH2:42]Cl)=[CH:38][CH:37]=2)=[CH:32][CH:31]=1)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]>O1CCCC1.CN(C)C=O.O>[CH2:22]([C:30]1[CH:31]=[CH:32][C:33]([C:36]2[CH:41]=[CH:40][C:39]([CH2:42][O:18][C:15]3[CH:14]=[CH:13][C:12]([O:11][CH2:10][CH:9]([O:8][C:6]([O:5][CH2:1][CH2:2][CH2:3][CH3:4])=[O:7])[CH3:19])=[CH:17][CH:16]=3)=[CH:38][CH:37]=2)=[CH:34][CH:35]=1)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 24758Sodium hydrideHCID 198182674'-Octyl-4-chloromethylbiphenylHCID 19818275p-(2-(Butoxycarbonyloxy)-propoxy)-phenol

Product 1

HCID 19818264HCID 19818264, compoundYield 24.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent
HCID 6228
Dimethylformamide
Solvent
HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of p-(2-(butoxycarbonyloxy)-propoxy)-phenol (1 g) prepared in Example 4 in tetrahydrofuran (20 ml) was dropwise added to a suspension of sodium hydride (0.2 g) in tetrahydrofuran, followed by dropwise adding to the mixture, a solution of 4'-octyl-4-chloromethylbiphenyl (1.2 g) in dimethylformamide (50 ml), agitating the mixture at 60° C. for 10 hours, pouring the reaction solution in water, extracting the resulting material with toluene (300 ml), washing the extract with an acid, then with an alkali and further with water, purifying it according to column chromatography using a column having activated alumina filled therein and recrystallizing from a mixed solvent of ethyl acetate with ethanol to obtain the objective 4'-octyl-4-(4-(2-(butoxycarbonyloxy)-propoxy)-phenoxymethyl)-biphenyl (0.5 g) having a m.p. of 94° C.

Workup

  1. additionby dropwise adding to the mixture
  2. extractionextracting the resulting material with toluene (300 ml)
  3. washwashing the
  4. extractionextract with an acid
  5. customwith an alkali and further with water, purifying it
  6. additionfilled
  7. customrecrystallizing from a mixed solvent of ethyl acetate with ethanol

Sources & evidence

ORD record
ord-5e0c92b01e0c4231878167099f95d9c7
Source dataset
uspto-grants-1991_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05032314

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes