Benzene → HCID 62397384, compound

HRID 1775992Notes

Reaction equation

HRID 1775992 reaction equation
[F:1][C:2]([F:12])([CH:6]([OH:11])[CH2:7][CH:8]([CH3:10])[CH3:9])[C:3]([OH:5])=[O:4].[CH2:13](O)[CH3:14].C1C=CC=CC=1>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>[F:1][C:2]([F:12])([CH:6]([OH:11])[CH2:7][CH:8]([CH3:10])[CH3:9])[C:3]([O:5][CH2:13][CH3:14])=[O:4]

Participants

6

Reactant 3

HCID 241BenzeneHCID 702EthanolHCID 57474515HCID 57474515, compound

Product 1

HCID 62397384HCID 62397384, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 962WaterSolvent

Procedure

To a mixture of 25.0 g of Intermediate 1 (Example 1), 20 g of ethanol and 200 g of benzene was added 0.15 g of p-toluenesulfonic acid monohydrate. With stirring in a nitrogen atmosphere, the mixture was heated for 20 hours while water of reaction was sequentially removed out of the system. After cooling, the reaction mixture was poured into a saturated sodium hydrogen carbonate aqueous solution and extracted with ethyl acetate. The ethyl acetate solution was washed, dried, and concentrated, obtaining 24.5 g (yield 85%) of crude ethyl 2,2-difluoro-3-hydroxy-5-methylhexanoate. This crude product had a sufficient purity as an intermediate and was ready for use in the subsequent step.

Workup

  1. customwas sequentially removed out of the system
  2. temperatureAfter cooling
  3. additionthe reaction mixture was poured into a saturated sodium hydrogen carbonate aqueous solution
  4. extractionextracted with ethyl acetate
  5. washThe ethyl acetate solution was washed
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-dea65e2c2153492fa2f4474d263e8b98
Source dataset
uspto-grants-2016_02
Patent number
US09261783B2

Reaction notes

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