Hydrochloric Acid → HCID 20304505, compound

HRID 236961Notes

Reaction equation

HRID 236961 reaction equation
[CH3:1][C:2]1[C:3](=[O:24])[C:4]2[CH:20]=[C:19]3[C:14]([CH2:15][CH2:16][CH2:17][CH2:18]3)=[C:13]([CH2:21][CH2:22][CH3:23])[C:5]=2[O:6][C:7]=1[C:8]([O:10]CC)=[O:9].Cl>C(O)(=O)C>[CH3:1][C:2]1[C:3](=[O:24])[C:4]2[CH:20]=[C:19]3[C:14]([CH2:15][CH2:16][CH2:17][CH2:18]3)=[C:13]([CH2:21][CH2:22][CH3:23])[C:5]=2[O:6][C:7]=1[C:8]([OH:10])=[O:9]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 20304565HCID 20304565, compound

Product 1

HCID 20304505HCID 20304505, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of the product of step (f) (16.2 g), glacial acetic acid (80 ml) and 5 N hydrochloric acid (20 ml) was heated and stirred on a steam bath overnight, and then evaporated. The residue was extracted with aqueous sodium bicarbonate and the extract was filtered and then acidified. Precipitated material was isolated by decantation and was triturated with water, dried, then triturated with an ether/petroleum ether (40°-60°) mixture. There remained as an insoluble off-white solid, 6,7,8,9-tetrahydro-3-methyl-4-oxo-10-propyl-4H-naphtho[2,3-b]pyran-2-carboxylic acid, (3.5 g), m.p 162°-4°.

Workup

  1. temperaturewas heated
  2. customevaporated
  3. extractionThe residue was extracted with aqueous sodium bicarbonate
  4. filtrationthe extract was filtered
  5. customPrecipitated material was isolated by decantation
  6. customwas triturated with water
  7. customdried
  8. customtriturated with an ether/petroleum ether (40°-60°) mixture
  9. customremained as an insoluble off-white solid, 6,7,8,9-tetrahydro-3-methyl-4-oxo-10-propyl-4H-naphtho[2,3-b]pyran-2-carboxylic acid, (3.5 g), m.p 162°-4°

Sources & evidence

ORD record
ord-32a39b1926d9437db97756beeb7c2a2c
Source dataset
uspto-grants-1979_06
Patent number
US04159273

Reaction notes

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