Phenol → HCID 19790041, compound

HRID 1656088Notes

Reaction equation

HRID 1656088 reaction equation
C[O:2][C:3]([C:5]1[C:6](C2C=CC=CC=2)=[CH:7][CH:8]=[CH:9][C:10]=1O)=[O:4].Br[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH:27]=[CH2:28].[H-].[Na+].C(OC(=O)[C@@H](O)C)C.C(OC1C=CC(O)=CC=1)C1C=CC=CC=1.[C:54]1([OH:60])[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1>CN(C=O)C.[Pd].N1C=CC=CC=1>[CH2:19]([O:60][C:54]1[CH:59]=[CH:58][C:57]([C:8]2[CH:7]=[CH:6][C:5]([C:3]([OH:4])=[O:2])=[CH:10][CH:9]=2)=[CH:56][CH:55]=1)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH:27]=[CH2:28]

Participants

10

Reactant 6

HCID 996PhenolHCID 7638MonobenzoneHCID 24758Sodium hydrideHCID 92831(L)-ethyl lactateHCID 54338410-Bromo-1-deceneHCID 14880641HCID 14880641, compound

Product 1

HCID 19790041HCID 19790041, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Procedure

The mesogenic group (R)-4'-(1-ethoxycarbonyl-1-ethoxy)-phenyl-4-[4-(9-decenyloxy)-phenyl]-benzoate 1 was synthesized as follows. 4'-(9-decenyloxy)biphenyl-4 carboxylic acid 1 was prepared by reacting hydroxybiphenyl carboxylic acid methyl ester with 10-bromo-1-decene in DMF containing NaH followed by hydrolysis. Compound 2 was synthesized by coupling of ethyl-(S)-2 hydroxypropionate with p-(benzyloxy)phenol. Hydrogenolysis of 2 by Palladium on activated charcoal led to the formation of the phenol derivative 3. The final product 1 was obtained by reaction of the acid chloride of 1 with 3 in the presence of pyridine.

Workup

  1. customThe mesogenic group (R)-4'-(1-ethoxycarbonyl-1-ethoxy)-phenyl-4-[4-(9-decenyloxy)-phenyl]-benzoate 1 was synthesized
  2. custom4'-(9-decenyloxy)biphenyl-4 carboxylic acid 1 was prepared
  3. customfollowed by hydrolysis

Sources & evidence

ORD record
ord-56c8318279ee474e8db477acda47b2ff
Source dataset
uspto-grants-1993_10
Patent number
US05252695

Reaction notes

Loading…