Hydrochloric Acid → HCID 20304505, compound

HRID 1732737Notes

Reaction equation

HRID 1732737 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-d5a167f06cdf446786503983b9b3e6f5
Source dataset
uspto-grants-1980_12
Patent number
US04238606

Reaction notes

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