Water → HCID 21536189, compound

HRID 1077294Notes

Reaction equation

HRID 1077294 reaction equation
[OH:1][CH2:2][C:3]1[C:4](=[O:17])[C:5]2[CH:16]=[C:15]3[C:10]([CH2:11][CH2:12][CH2:13][CH2:14]3)=[CH:9][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]=[C:15]3[C:10]([CH2:11][CH2:12][CH2:13][CH2:14]3)=[CH:9][C:6]=2[O:7][CH:8]=1)=[O:1]

Participants

5

Reactant 3

HCID 962WaterHCID 108005Sodium dichromate dihydrateHCID 21536179HCID 21536179, compound

Product 1

HCID 21536189HCID 21536189, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
60 °C

Procedure

A mixture of 2.3 g (0.01 mole) of 3-(hydroxymethyl)-6,7,8,9-tetrahydro-4H-naphtho[2,3-b]pyran-4-one and 15 ml of glacial acetic acid is added to a solution of 2.98 g (0.01 mole) of sodium dichromate dihydrate in 15 ml of glacial acetic acid, keeping the temperature at about 50°C. with mild cooling. After 15 minutes, the reaction is heated at 60°C. for 15 minutes, water (100 ml) is added and the mixture is heated at 50°C. for 5 minutes. The separated solid is filtered, washed with water and dried; wt. 1.6 g (70%); mp 120°-123°C. Purification is effected by dissolving in methylene chloride and filtering through a layer of silica gel. The pure aldehyde is obtained by removal of solvent from the filtrate; mp 128°-130°C.

Workup

  1. customat about 50°C.
  2. temperaturethe mixture is heated at 50°C. for 5 minutes
  3. filtrationThe separated solid is filtered
  4. washwashed with water
  5. customdried
  6. customPurification
  7. dissolutionby dissolving in methylene chloride
  8. filtrationfiltering through a layer of silica gel

Sources & evidence

ORD record
ord-b87858681ef5438b9c08f8758a440c2c
Source dataset
uspto-grants-1976_05
Patent number
US03959480

Reaction notes

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