Potassium Hydroxide → HCID 69236154, compound

HRID 1593618Notes

Reaction equation

HRID 1593618 reaction equation
[CH2:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[S:6][C:5]=2[CH2:4][CH2:3][CH:2]1[C:14]([O:16]CC)=[O:15].[OH-].[K+]>CCO>[CH2:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[S:6][C:5]=2[CH2:4][CH2:3][CH:2]1[C:14]([OH:16])=[O:15]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 58999633HCID 58999633, compound

Product 1

HCID 69236154HCID 69236154, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of ethyl 1,2,3,4-tetrahydrodibenzo[b,d]thiophene-2-carboxylate (1.15 g, 4.42 mmol) in EtOH (50 mL) was added KOH (0.4 g, 7.07 mmol). The reaction was stirred at 40° C. for 3 hours. After cooling to room temperature, the mixture was extracted with ether. The ether layer was washed with aqueous Na2CO3. The combined aqueous layers were acidified to pH 2 with conc. HCl and extracted with EtOAc. The EtOAc layer was washed with brine, then was dried over MgSO4 and concentrated to dryness to afford the 0.77 g (75%) of the title compound as a white solid: mp 202-203° C., MS (−) 231 (M−H)−.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionthe mixture was extracted with ether
  3. washThe ether layer was washed with aqueous Na2CO3
  4. extractionextracted with EtOAc
  5. washThe EtOAc layer was washed with brine
  6. dry with materialwas dried over MgSO4
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-a4d2647a5e1c4797be6ae5c1c75d4fda
Source dataset
uspto-grants-2007_11
Patent number
US07297704B2

Reaction notes

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