Sodium Hydroxide → HCID 74538749, compound

HRID 1500152Notes

Reaction equation

HRID 1500152 reaction equation
COC([C:5]1([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)[CH2:9][CH2:8][C:7]2([CH2:14][O:13][C:12]([CH3:16])([CH3:15])[O:11][CH2:10]2)[C:6]1=[O:17])=O.[OH-].[Na+]>C1(C)C=CC=CC=1>[Cl:25][C:22]1[CH:23]=[CH:24][C:19]([CH2:18][CH:5]2[CH2:9][CH2:8][C:7]3([CH2:10][O:11][C:12]([CH3:16])([CH3:15])[O:13][CH2:14]3)[C:6]2=[O:17])=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 90097014HCID 90097014, compound

Product 1

HCID 74538749HCID 74538749, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

After adding toluene (1 mL) in 2-(4-chlorobenzyl)-8,8-dimethyl-1-oxo-7,9-dioxaspiro[4.5]decane-2-carboxylic acid methyl ester (10.0 g, 0.0273 mol), the mixture was suspended in a 0.5 M sodium hydroxide solution (27.3 mL, 0.0273 mol×0.5 mol) and reacted at 110° C. The reaction was continued by adding a 0.5 M sodium hydroxide solution (27.3 mL, 0.0273 mol×0.5 mol) every 2 hours (for three times total), and heating and stirring were performed for total of 9 hours. Following the completion of the reaction, the mixture was allowed to cool to room temperature and then subjected to extraction using toluene. The organic layer was washed with saturated brine solution, and then dried using anhydrous sodium sulfate. Thereafter, the dried product was purified using a silica gel column, and a target product was obtained.

Workup

  1. customreacted at 110° C
  2. temperatureheating
  3. customwere performed for total of 9 hours
  4. customthe completion of the reaction
  5. extractionsubjected to extraction
  6. washThe organic layer was washed with saturated brine solution
  7. customdried
  8. customThereafter, the dried product was purified
  9. customa target product was obtained

Sources & evidence

ORD record
ord-ec0bcb22f7a04efba7c5f7ec76100d1a
Source dataset
uspto-grants-2015_12
Patent number
US09206106B2

Reaction notes

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