Benzene → HCID 86663804, compound

HRID 1775993Notes

Reaction equation

HRID 1775993 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].[CH3:13][O:14][CH2:15][CH2:16]O.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][CH2:16][CH2:15][O:14][CH3:13])=[O:4]

Participants

6

Reactant 3

HCID 241BenzeneHCID 80192-MethoxyethanolHCID 57474515HCID 57474515, compound

Product 1

HCID 86663804HCID 86663804, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 962WaterSolvent

Procedure

To a mixture of 25.0 g of Intermediate 1 (Example 1), 25 g of 2-methoxyethanol 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 8 hours while water of reaction was sequentially removed out of the system. After cooling, the reaction mixture was poured into ice water and extracted with ether. The ether solution was washed, dried, and concentrated, obtaining 23.9 g (yield 73%) of crude 2-methoxyethyl 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 ice water
  4. extractionextracted with ether
  5. washThe ether solution was washed
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8feb188f7c8e4ce981dd446704819ea1
Source dataset
uspto-grants-2016_02
Patent number
US09261783B2

Reaction notes

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