Hydrochloric Acid → HCID 44549144, compound

HRID 2238409Notes

Reaction equation

HRID 2238409 reaction equation
[OH-].[K+].[C:3]([C:6]1[CH:15]=[C:14]2[C:9]([CH:10]=[CH:11][C:12]([C:16]([O:18]C)=[O:17])=[CH:13]2)=[CH:8][CH:7]=1)(=[O:5])[CH3:4].Cl>O.CO.C(Cl)Cl>[C:3]([C:6]1[CH:15]=[C:14]2[C:9]([CH:10]=[CH:11][C:12]([C:16]([OH:18])=[O:17])=[CH:13]2)=[CH:8][CH:7]=1)(=[O:5])[CH3:4]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 44549143HCID 44549143, compound

Product 1

HCID 44549144HCID 44549144, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

A solution of KOH 70 mg, 10 mmol) in water (3.5 mL) was added dropwise to a cooled solution of the ester 168 (640 mg, 2.81 mmol) in MeOH (10 mL) and CH2Cl2 (10 mL) at 0° C. After allowing the mixture to warm to room temperature and stirring for 96 h, excess CH2Cl2 and water were added. The aqueous portion was acidified (pH 2) with 2N HCl and the resulting white precipitate was extracted with EtOAc (×2). The combined EtOAc extracts were washed with water, brine, and dried, to give 7-acetyl-2-naphthoic acid (169). (575 mg, 96%) as a colorless solid. A sample was recrystallised from petroleum ether/CH2Cl2/Et2O: mp 224-228° C.; 1H NMR: (CDCl3) 8 (CO2H not observed) 8.82 (s, 1H), 8.60 (s, 1H), 8.23 (dd, J=8.6, 1.6 Hz, 1H), 8.18 (dd, J=8.7, 1.7 Hz, 1H), 7.97 (c, J=8.7 Hz, 2H), 2.76 (s, 3H). Anal. (C13H10O3) C, H.

Workup

  1. extractionthe resulting white precipitate was extracted with EtOAc (×2)
  2. washThe combined EtOAc extracts were washed with water, brine
  3. customdried

Sources & evidence

ORD record
ord-b597d04197564f69a69895a0aaf4a27c
Source dataset
uspto-grants-2010_05
Patent number
US07718688B2

Reaction notes

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