Toluene → HCID 178444584, compound

HRID 845007Notes

Reaction equation

HRID 845007 reaction equation
[CH2:1]([C@@H:6]1[CH2:11][O:10][C@@H:9](C2C=CC=CC=2C(O)=O)[CH2:8][O:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].[O:21]=S(Cl)Cl.[C:25]1([CH3:31])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[CH2:32]([C@H:37]1[CH2:42][CH2:41][C@H:40]([OH:43])[CH2:39][CH2:38]1)[CH2:33][CH2:34][CH2:35][CH3:36]>N1C=CC=CC=1>[CH2:32]([C@H:37]1[CH2:38][CH2:39][C@H:40]([O:43][C:31](=[O:21])[C:25]2[CH:30]=[CH:29][C:28]([C@H:9]3[CH2:8][O:7][C@H:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[CH2:11][O:10]3)=[CH:27][CH:26]=2)[CH2:41][CH2:42]1)[CH2:33][CH2:34][CH2:35][CH3:36]

Participants

6

Reactant 4

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 70419040HCID 70419040, compoundHCID 178444573HCID 178444573, compound

Product 1

HCID 178444584HCID 178444584, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

One boils 27.8 g. (trans-5-pentyl-1,4-dioxanyl)-benzoic acid (obtainable by reaction of trans-2-phenyl-5-pentyl-1,4-dioxane with CH3COCl/AlCl3 to give 2-p-acetylphenyl-5-pentyl-1,4-dioxane and decomposition with bromine/KOH) for 1 hour with 24 g. SOCl2, dissolves the crude acid chloride obtained in 150 ml. toluene, mixes with 8 ml. pyridine and 16.6 g. trans-4-pentylcyclohexanol and boils for 2 hours. After cooling and usual working up, one obtains p-(trans-5-pentyl-1,4-dioxan-2-yl)-benzoic acid trans-4-pentylcyclohexyl ester.

Workup

  1. customobtained in 150 ml
  2. temperatureAfter cooling

Sources & evidence

ORD record
ord-f461400f4781475895c833a03bd31bf4
Source dataset
uspto-grants-1988_07
Patent number
US04755323

Reaction notes

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