Sulfuric Acid → HCID 20393454, compound

HRID 1973746Notes

Reaction equation

HRID 1973746 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[C:13]([C:16]1([CH3:22])[O:21][C:19](=[O:20])[CH2:18][CH2:17]1)(O)=[O:14]>CCOCC>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:13]([C:16]2([CH3:22])[O:21][C:19](=[O:20])[CH2:18][CH2:17]2)=[O:14])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 10008FluorobenzeneHCID 15109407HCID 15109407, compound

Product 1

HCID 20393454HCID 20393454, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
10 °C

Procedure

To 0.5 moles of fluorobenzene and 0.2 moles of sulfuric acid at 80° C is added portionwise 0.2 , moles of gamma-carboxy-gamma-valerolactone (I). The mixture is kept at 80° C for an additional hour. The mixture is cooled to 10° C and 100 ml of ether is added. The mixture is poured onto ice and 100 ml of ether is added. The layers are separated and the aqueous layer is back extracted with ether and the ether extracts are combined. The combined ether extracts are washed with water, saturated sodium bicarbonate (twice), water, dried and concentrated to give the crude product (III).

Workup

  1. waitThe mixture is kept at 80° C for an additional hour
  2. additionis added
  3. customThe layers are separated
  4. extractionthe aqueous layer is back extracted with ether
  5. washThe combined ether extracts are washed with water, saturated sodium bicarbonate (twice), water
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c2a8efcc85a94d698d34bd6904d23d62
Source dataset
uspto-grants-1976_12
Patent number
US03998875

Reaction notes

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