Sodium Hydroxide → HCID 18518698, compound

HRID 1385981Notes

Reaction equation

HRID 1385981 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][C:11]2([OH:19])[C:14]([O:16]CC)=[O:15])=[CH:6][CH:5]=1>CS(C)=O.[Cl-].[Na+].O>[Cl:3][C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][C:11]2([OH:19])[C:14]([OH:16])=[O:15])=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 70011081HCID 70011081, compound

Product 1

HCID 18518698HCID 18518698, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
100 °C

Procedure

NaOH (10M, 1 mL) was added to a solution of 7-chloro-1-hydroxytetraline-1-carboxylic acid, ethyl ester (0.8 g; 3.1 mmol; from step (iii) above) in DMSO (20 mL), and the mixture was heated to 100° C. for 3 hours. The resultant mixture was diluted with crushed ice (40 g) and brine (40 mL), and the mixture was extracted with EtOAc. The aqueous layer was acidified to pH 2 with 2M HCl and extracted with EtOAc (2×40 mL). The combined organic layer was dried (Na2SO4) and concentrated. Yield 0.22 mg (30%).

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. extractionextracted with EtOAc (2×40 mL)
  3. dry with materialThe combined organic layer was dried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-440f2e1a76ee4bc7a2abe26e9ba71dcc
Source dataset
uspto-grants-2001_07
Patent number
US06265397B1

Reaction notes

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