Hydrochloric Acid → HCID 21883633, compound

HRID 722296Notes

Reaction equation

HRID 722296 reaction equation
FC(F)(F)C1CO[C:6]2[CH:19]=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:7]=2C=1C(O)=O.[F:22][C:23]([F:44])([F:43])[C:24]1COC2C=CC3C(=CC=CC=3)[C:28]=2[C:29]=1[C:30]([O:32]CC)=[O:31].[OH-:45].[Na+].Cl>C(O)C.O1CCCC1>[F:22][C:23]([F:44])([F:43])[CH:24]1[O:45][C:7]2[C:12]3[C:17]([CH:18]=[CH:19][C:6]=2[CH:28]=[C:29]1[C:30]([OH:32])=[O:31])=[CH:16][CH:15]=[CH:14][CH:13]=3

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 53638824HCID 53638824, compoundHCID 69662645HCID 69662645, compound

Product 1

HCID 21883633HCID 21883633, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 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-617dab899ffd4615b502ab9fe49fd7b1
Source dataset
uspto-grants-2006_11
Patent number
US07138411B2

Reaction notes

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