Water → HCID 21536183, compound

HRID 1077295Notes

Reaction equation

HRID 1077295 reaction equation
[OH:1][CH2:2][C:3]1[C:4](=[O:17])[C:5]2[CH:16]=[CH:15][C:14]3[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=3[C:6]=2[O:7][CH:8]=1.O.O.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[Na+].[Na+].O>C(O)(=O)C>[CH:2]([C:3]1[C:4](=[O:17])[C:5]2[CH:16]=[CH:15][C:14]3[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=3[C:6]=2[O:7][CH:8]=1)=[O:1]

Participants

5

Reactant 3

HCID 962WaterHCID 108005Sodium dichromate dihydrateHCID 21536177HCID 21536177, compound

Product 1

HCID 21536183HCID 21536183, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
60 °C

Procedure

This compound is prepared by adding a mixture of 23.0 g (0.1 mole) of 3-(hydroxymethyl)-7,8,9,10-tetrahydro-4H-naphtho-[1,2-b]pyran-4-one and 150 ml of glacial acetic acid to a solution of 29.8 g (0.1 mole) of sodium dichromate dihydrate in 150 ml of glacial acetic acid, keeping the temperature at about 50°C with cooling. After the initial exotherm, the reaction is heated at 60°C for one-half hour, water (1-liter) is added, and the mixture is heated at 75°C for about one-half hour to generate a precipitate. The cooled mixture is filtered and the crude product is purified by dissolving in methylene chloride and filtering through a layer of silica gel. The aldehyde is obtained by removal of solvent from the filtrate. ##SPC32##

Workup

  1. customThis compound is prepared
  2. additionby adding
  3. customat about 50°C
  4. temperaturewith cooling
  5. temperaturethe mixture is heated at 75°C for about one-half hour
  6. filtrationThe cooled mixture is filtered
  7. customthe crude product is purified
  8. dissolutionby dissolving in methylene chloride
  9. filtrationfiltering through a layer of silica gel

Sources & evidence

ORD record
ord-3d847c82e1ca4b5b9649772e555637cc
Source dataset
uspto-grants-1976_05
Patent number
US03959480

Reaction notes

Loading…