Sulfuric Acid → HCID 20450693, compound

HRID 1463016Notes

Reaction equation

HRID 1463016 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[CH2:11][OH:12].[CH:13](=O)[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].S(=O)(=O)(O)O>C1C=CC=CC=1>[CH2:14]([CH:13]1[O:1][C:2]2[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=2[CH2:11][O:12]1)[CH2:15][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 6184HexanalHCID 144020314-Hydroxy-3-hydroxymethyl-benzoic acid

Product 1

HCID 20450693HCID 20450693, compoundYield 46.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 16.8 g of 4-hydroxy-3-(hydroxymethyl)-benzoic acid, 1000 ml of benzene, 15.0 g of caproaldehyde and 0.36 ml of concentrated sulphuric acid is boiled for 5 hours while stirring under a water separator. After cooling, the mixture is filtered. The filtrate is concentrated and the residue is boiled up with hexane. The insoluble material is dissolved in ether/hexane and stirred up in the cold with active carbon. The mixture is filtered, the filtrate is evaporated and the residue is boiled with isopropyl ether. There are obtained 11.7 g of beige colored 2-pentyl-1,3-benzodioxan-6-carboxylic acid; m.p. 148° C.

Workup

  1. temperatureAfter cooling
  2. filtrationthe mixture is filtered
  3. concentrationThe filtrate is concentrated
  4. dissolutionThe insoluble material is dissolved in ether/hexane
  5. stirringstirred up in the cold with active carbon
  6. filtrationThe mixture is filtered
  7. customthe filtrate is evaporated

Sources & evidence

ORD record
ord-0e325c79f6f347a5a154bed921b6aea1
Source dataset
uspto-grants-1984_07
Patent number
US04462923

Reaction notes

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