Benzene → HCID 86663804, compound

HRID 2367716Notes

Reaction equation

HRID 2367716 reaction equation
[F:1][C:2]([F:18])([CH:7]([O:12]C(=O)C(C)=C)[CH2:8][CH:9]([CH3:11])[CH3:10])[C:3]([O:5][CH3:6])=[O:4].[CH3:19][O:20][CH2:21]CO.C1C=CC=CC=1>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>[F:18][C:2]([F:1])([CH:7]([OH:12])[CH2:8][CH:9]([CH3:10])[CH3:11])[C:3]([O:5][CH2:6][CH2:19][O:20][CH3:21])=[O:4]

Participants

6

Reactant 3

HCID 241BenzeneHCID 80192-MethoxyethanolHCID 86663802HCID 86663802, compound

Product 1

HCID 86663804HCID 86663804, compoundYield 105.2%

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-23ac4b490ded4f8fb81b11ec0ca7da2c
Source dataset
uspto-grants-2014_04
Patent number
US08697903B2

Reaction notes

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