Sulfuric Acid → HCID 178501284, compound

HRID 1516150Notes

Reaction equation

HRID 1516150 reaction equation
[OH:1][C@@H:2]1[CH2:7][CH2:6][C@H:5]([C:8]([OH:10])=[O:9])[CH2:4][CH2:3]1.S(=O)(=O)(O)O.[C:16](=O)([O-])[O-].[Na+].[Na+]>CO>[CH3:16][O:9][C:8]([C@H:5]1[CH2:6][CH2:7][C@@H:2]([OH:1])[CH2:3][CH2:4]1)=[O:10]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 178525779HCID 178525779, compound

Product 1

HCID 178501284HCID 178501284, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of cis-4-hydroxy-cyclohexanecarboxylic acid (10.0 g, 69.4 mmol) and a catalytic amount of concentrated sulfuric acid in methanol (700 ml) was heated at reflux over night. After cooling to room temperature the reaction mixture was neutralized by the addition of solid sodium carbonate. The mixture was stirred for 30 min, filtered and concentrated in vacuo. The residue was triturated in ethyl acetate (150 ml). The solids were removed by filtration. The filtrate was concentrated in vacuo to give the crude product (10.3 g, 94%) as colorless oil, which was used in the following steps without further purification. MS m/e: 159 (M+H+).

Workup

  1. temperatureat reflux over night
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. customThe residue was triturated in ethyl acetate (150 ml)
  5. customThe solids were removed by filtration
  6. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-e928e8f2d5ef4a72b80aa567dde9d2fe
Source dataset
uspto-grants-2012_07
Patent number
US08227458B2

Reaction notes

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