Pimelic Acid → HCID 13120336, compound

HRID 2412383Notes

Reaction equation

HRID 2412383 reaction equation
CO[CH:3](COCCCCCCCC1C=CC(CCCCCCCC)=CC=1)[CH2:4]O.[CH2:29]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36].[C:43]([OH:53])(=O)[CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][C:49]([OH:51])=[O:50].[Cl-].[Al+3].[Cl-].[Cl-]>[N+](C1C=CC=CC=1)([O-])=O>[CH2:3]([O:51][C:49](=[O:50])[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44][C:43]([C:40]1[CH:39]=[CH:38][C:37]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])=[CH:42][CH:41]=1)=[O:53])[CH3:4]

Participants

6

Reactant 4

HCID 385Pimelic AcidHCID 16607OctylbenzeneHCID 6451240Aluminum(III) ChlorideHCID 20432203HCID 20432203, compound

Product 1

HCID 13120336HCID 13120336, compound

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Procedure

The 2-methoxy-3-[7-(4-octylphenyl)-heptyloxy]-1-propanol used as starting material is obtained in the following manner: 4-octylbenzene is reacted with the ethyl ester acid chloride of pimelic acid in the presence of aluminium chloride in nitrobenzene to give 7-(4-octylphenyl)-7-oxoheptanoic acid ethyl ester (m.p. 38°-40° C.). Subsequent hydrogenation in the presence of palladium on charcoal in ethanol with the addition of some perchloric acid gives 7-(4-octylphenyl)-heptanoic acid ethyl ester (oily substance), reduction of which with lithium aluminium hydride gives 7-(4-octylphenyl)-heptanol (oily substance). Reaction with phosphorus tribromide gives the corresponding bromide (oil) which is reacted with the monosodium salt of 2-methoxy-1,3-propandiol.

Workup

  1. customis obtained in the following manner

Sources & evidence

ORD record
ord-2b0945efff9843bba248aa36400df7cf
Source dataset
uspto-grants-1985_01
Patent number
US04492659

Reaction notes

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