Hydrochloric Acid → HCID 69662645, compound

HRID 1636652Notes

Reaction equation

HRID 1636652 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH2:4][O:5][C:6]2[CH:19]=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:7]=2[C:8]=1[C:9]([OH:11])=[O:10].[OH-].[Na+].Cl.[CH2:25](O)[CH3:26]>O1CCCC1>[F:21][C:2]([F:1])([F:20])[C:3]1[CH2:4][O:5][C:6]2[CH:19]=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:7]=2[C:8]=1[C:9]([O:11][CH2:25][CH3:26])=[O:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 53638824HCID 53638824, compound

Product 1

HCID 69662645HCID 69662645, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Preparation of 2-trifluoromethyl-3H-naphthopyran-carboxylic acid. A solution of the ester from Step 1 (0.8 g, 2.5 mmol) was dissolved in 40 mL of ethanol and 10 mL of tetrahydrofuran, treated with sodium hydroxide (2.5 N, 10 mL, 25 mmol) and stirred at room temperature for 16 hours. The reaction mixture was acidified with 1.0 N HCl, whereupon a solid formed that was isolated by filtration. The solid was washed with 20 mL of water to afford 0.7 g (95%) of the title compound as a yellow solid: mp 245.9-248.6° C. 1H NMR (acetone-d6 /300 MHz) 8.57 (s, 1H), 8.28 (d, 1H, J=8.7 Hz), 8.03 (d, 1H, J=9.0 Hz), 7.93 (d, 1H, J=8.7), 7.67 (m, 1H), 7.50 (m, 1H), 7.28 (d, 1H, J=9.0), 5.96 (qH-F, 1H, J=7.2 Hz). FABHRMS m/z 295.0561 (M+H, Calc'd 295.0582). Anal. Calc'd for C15H9O3F3 +3.31% H2O: C, 59.21; H, 3.35. Found: C, 59.17; H, 3.07.

Workup

  1. customformed that
  2. customwas isolated by filtration
  3. washThe solid was washed with 20 mL of water

Sources & evidence

ORD record
ord-79e983a703a042898364e1e374429ee2
Source dataset
uspto-grants-2000_03
Patent number
US06034256

Reaction notes

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