Hydrochloric Acid → HCID 66862822, compound

HRID 1921247Notes

Reaction equation

HRID 1921247 reaction equation
[OH-].[K+].C[O:4][C:5]([CH:7]1[CH2:16][C:15]2[C:10](=[CH:11][C:12]([O:17][CH3:18])=[CH:13][CH:14]=2)[CH2:9][S:8]1)=[O:6].Cl>CO.O>[CH3:18][O:17][C:12]1[CH:11]=[C:10]2[C:15]([CH2:16][CH:7]([C:5]([OH:6])=[O:4])[S:8][CH2:9]2)=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 66862732HCID 66862732, compound

Product 1

HCID 66862822HCID 66862822, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

Potassium hydroxide (0.80 g, 14.3 mmol) was added to a solution of 7-methoxy-isothiochroman-3-carboxylic acid methyl ester (0.34 g, 1.43 mmol) in MeOH (50 mL). The solution was heated at 60° C. for 2 h, cooled to room temperature, and diluted with H2O (100 mL). The solution was made acidic with 6 M HCl and extracted with EtOAc (3×100 mL). The organic extracts were combined, dried (MgSO4) and concentrated to give 7-methoxy-isothiochroman-3-carboxylic acid (0.28 g, 88%) as a pale yellow solid. The solid was used in the next step without further purification.

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with EtOAc (3×100 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2e913c1aa4f346c6af7596af3a5ccfba
Source dataset
uspto-grants-2012_05
Patent number
US08173678B2

Reaction notes

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