Methanol → HCID 69982964, compound

HRID 2231113Notes

Reaction equation

HRID 2231113 reaction equation
CC1[CH:3]=[C:4]([C:7]2[C:8]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[C:9]([C:13]([CH:15]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)[OH:16])=[O:14])[CH:10]=[CH:11][CH:12]=2)SC=1.O[O:31][S:32]([O-:34])=O.[K+].O1[CH2:40][CH2:39][CH2:38][CH2:37]1.O.[CH3:42]O>C(Cl)Cl>[CH3:42][S:32]([C:38]1[CH:39]=[CH:40][C:4]([C:7]2[C:8]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)=[C:9]([C:13]([CH:15]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)[OH:16])=[O:14])[CH:10]=[CH:11][CH:12]=2)=[CH:3][CH:37]=1)(=[O:34])=[O:31]

Participants

7

Reactant 5

HCID 887MethanolHCID 962Water2×HCID 8028TetrahydrofuranHCID 23707502Potassium hydroxy sulfiteHCID 69984876HCID 69984876, compound

Product 1

HCID 69982964HCID 69982964, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The sulfone was synthesized according to the procedure of Example 41, Step 4 using the product of Step 1 (1.8 g, 6.5 mmol) and Oxone® (10 g, 15 mmol) in methanol (125 ml), tetrahydrofuran (50 ml) and water (50 ml). Because of its water solubility, methylene chloride was used to extract the product from the aqueous reaction mixture. There was isolated 2.25 g (98%) of the desired benzoin as a crystalline solid: mp 106-107° C. Anal. Calc'd. for C15H13OF4S (MW 308.33): C, 58.43; H, 4.25; S, 10.40. Found: C, 58.22; H, 4.12; S, 10.70.

Workup

  1. customThe sulfone was synthesized
  2. extractionto extract the product from the aqueous reaction mixture

Sources & evidence

ORD record
ord-974d37bdf6594bdf9d0a890dbec6fb68
Source dataset
uspto-grants-2002_07
Patent number
US06426360B1

Reaction notes

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