Sulfuric Acid → HCID 4518867, compound

HRID 1612387Notes

Reaction equation

HRID 1612387 reaction equation
[BH4-].[Na+].[CH:3]12[CH2:9][CH:6]([CH:7]=[CH:8]1)[CH:5]1[C:10]([O:12][C:13](=O)[CH:4]21)=[O:11].S(=O)(=O)(O)O>C1COCC1.CO>[CH:6]12[CH2:9][CH:3]([CH2:8][CH2:7]1)[CH:4]1[CH:5]2[C:10](=[O:11])[O:12][CH2:13]1

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 13223826-62-0HCID 4311764Sodium borohydride

Product 1

HCID 4518867HCID 4518867, compoundYield 64.76%

Reagents, catalysts & solvents 2

HCID 887MethanolCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
30 °C

Procedure

Under nitrogen atmosphere, 176 g (4.649 mol) of sodium borohydride was put into a flask and 2000 g of THF and 9.8 g of methanol were added thereto. A solution of 954 g (5.812 mol) of 5-norbornene-2,3-dicarboxylic anhydride dissolved in 2800 g of THF was added thereto dropwise while cooling them by an ice bath to keep the reaction temperature at 35° C. or lower. After completion of the dropping, the mixture was stirred at 30° C. for 4 hours, then poured into 3000 g of 10% aqueous sulfuric acid solution at 20° C. or lower and stirred for a while. Under reduced pressure, THF was recovered, and 1800 g of MIBK was added thereto for extraction. Further 900 g of MIBK was added to the separated aqueous layer for extraction and combined with the organic layer. 63.6 g of sodium carbonate and 200 g of water were added to the organic layer and stirred for a while. The separated organic layer was washed with diluted sulfuric acid and water, then concentrated, thereby 565.3 g of a white solid desired product of a lactone compound was obtained (64.76% yield).

Workup

  1. additionwas added
  2. temperaturedropwise while cooling them by an ice bath
  3. customat 35° C.
  4. stirringlower and stirred for a while
  5. customUnder reduced pressure, THF was recovered
  6. addition1800 g of MIBK was added
  7. extractionfor extraction
  8. additionFurther 900 g of MIBK was added to the separated aqueous layer for extraction
  9. addition63.6 g of sodium carbonate and 200 g of water were added to the organic layer
  10. stirringstirred for a while
  11. washThe separated organic layer was washed with diluted sulfuric acid and water
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-b890ae07178b41cdb3e1161c008e7d24
Source dataset
uspto-grants-2006_01
Patent number
US06992197B2

Reaction notes

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