Formic Acid → HCID 178501095, compound

HRID 726450Notes

Reaction equation

HRID 726450 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([C@H:11]2[CH2:16][CH2:15][C@H:14]([C@H:17]3[CH2:22][CH2:21][C@H:20]([CH2:23][CH2:24][CH:25]4OCCC[O:26]4)[CH2:19][CH2:18]3)[CH2:13][CH2:12]2)[CH2:7][CH2:6]1)=[O:4].C(O)=O>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]([C@H:5]1[CH2:6][CH2:7][C@H:8]([C@H:11]2[CH2:16][CH2:15][C@H:14]([C@H:17]3[CH2:22][CH2:21][C@H:20]([CH2:23][CH2:24][CH:25]=[O:26])[CH2:19][CH2:18]3)[CH2:13][CH2:12]2)[CH2:9][CH2:10]1)=[O:4]

Participants

4

Reactant 2

HCID 284Formic AcidHCID 178501094HCID 178501094, compound

Product 1

HCID 178501095HCID 178501095, compoundYield 74.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 140 g (333 mmol) of trans-4-(trans-4-(trans-4-(2-(1,3-dioxane-2-yl)ethyl)cyclohexyl)cyclohexyl)cyclohexane carboxylic acid methyl ester dissolved in 1.5 liters of toluene were added 153 g (3330 mmol) of formic acid and the mixture was heated under reflux for one hour. The reaction solution was washed three times with 500 ml of an aqueous saturated sodium carbonate and then with 750 ml of water, and dried over anhydorus magnesium sulfate. Distilling off the solvent under reduced pressure gave 90.0 g of crude trans-4-(trans-4-(trans-4-(2-formylethyl)cyclohexyl)-cyclohexyl)cyclohexane carboxylic acid methyl ester.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for one hour
  3. washThe reaction solution was washed three times with 500 ml of an aqueous saturated sodium carbonate
  4. dry with materialwith 750 ml of water, and dried over anhydorus magnesium sulfate
  5. distillationDistilling off the solvent under reduced pressure

Sources & evidence

ORD record
ord-fa7102f1dcd74d238d23246ef4eb241c
Source dataset
uspto-grants-1998_01
Patent number
US05709820

Reaction notes

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