Toluene → HCID 23671748, compound

HRID 2211259Notes

Reaction equation

HRID 2211259 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][C:12]2([C:18]([O:20]C)=[O:19])[CH2:17][CH2:16][CH:15]=[CH:14][CH2:13]2)=[CH:4][CH:3]=1.[OH-].[Na+:23].C1(C)C=CC=CC=1.CCCCCCC>CO.O1CCOCC1.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][C:12]2([C:18]([O-:20])=[O:19])[CH2:17][CH2:16][CH:15]=[CH:14][CH2:13]2)=[CH:6][CH:7]=1.[Na+:23]

Participants

8

Reactant 4

HCID 1140TolueneHCID 8900HeptaneHCID 14798Sodium HydroxideHCID 19376295HCID 19376295, compound

Product 1

HCID 23671748HCID 23671748, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

22.7 g of methyl 1-[4-(4-chlorophenyl)butyl]cyclohex-3-ene-1-carboxylate 70B are dissolved in 100ml of methanol +100 ml of dioxane. To this is added a solution of 8 g of sodium hydroxide in 50 ml of water, and the mixture is refluxed under protective gas for 16 h. The reaction solution is cooled and 200 ml of water, 100 ml of toluene and 100 ml of n-heptane are added, and the mixture is stirred thoroughly. The precipitated product is filtered off with suction, washed with a little cold water and n-heptane/toluene (1:1 vol/vol) and dried in vacuo. 70C of the formula ##STR34## is obtained as colorless shining flakes which do not melt up to 240° C. The free acid obtained from the sodium salt 70C by acidification with concentrated hydrochloric acid melts at 86°-7° C.

Workup

  1. temperaturethe mixture is refluxed under protective gas for 16 h
  2. temperatureThe reaction solution is cooled
  3. filtrationThe precipitated product is filtered off with suction
  4. washwashed with a little cold water and n-heptane/toluene (1:1 vol/vol)
  5. customdried in vacuo

Sources & evidence

ORD record
ord-a74b9e79471a4fb1bfc239bb3c06fae9
Source dataset
uspto-grants-1995_10
Patent number
US05463062

Reaction notes

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