Methanol → HCID 69982908, compound

HRID 2231110Notes

Reaction equation

HRID 2231110 reaction equation
O[O:2][S:3]([O-:5])=O.[K+].[CH3:7][C:8]1[CH:9]=[C:10]([C:13]2[C:14]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[C:15]([C:19]([C:21]([C:23]3[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([O:31][CH3:32])[CH:24]=3)=[O:22])=[O:20])[CH:16]=[CH:17][CH:18]=2)SC=1.[CH3:39]O.O1CC[CH2:43][CH2:42]1>O>[CH3:39][S:3]([C:7]1[CH:8]=[CH:9][C:10]([C:13]2[C:14]([C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)=[C:15]([C:19]([C:21]([C:23]3[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([O:31][CH3:32])[CH:24]=3)=[O:22])=[O:20])[CH:16]=[CH:17][CH:18]=2)=[CH:43][CH:42]=1)(=[O:5])=[O:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 23707502Potassium hydroxy sulfiteHCID 69983437HCID 69983437, compound

Product 1

HCID 69982908HCID 69982908, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
40 °C

Procedure

A solution of Oxone®(9.8 g, 16 mmol) in water (50 ml) was added dropwise over 15 minutes to a solution of the benzil from Step 3 (2.0 g, 63 mmol) in a methanol:tetrahydrofuran solution (2:1, 100 ml). The reaction mixture was warmed to 40° C. for 2 hours, cooled and poured into water (500 ml). The solid precipitate was filtered and air dried to give 2.0 g (95%) of desired product as a solid: mp 181-183° C. Anal. Calc'd. for C17H16O6S (MW 348.38): C, 58.61; H, 4.63; S, 9.20. Found: C, 58.55; H, 4.49; S, 9.29.

Workup

  1. temperaturecooled
  2. filtrationThe solid precipitate was filtered
  3. customair dried

Sources & evidence

ORD record
ord-17ec604873b844389e88c149525773c1
Source dataset
uspto-grants-2002_07
Patent number
US06426360B1

Reaction notes

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