Isopropanol → HCID 86739368, compound

HRID 615720Notes

Reaction equation

HRID 615720 reaction equation
[Br:1][C:2]([C@H:5]1[C@H:9]([OH:10])[O:8][C:7](=[O:11])[CH2:6]1)([CH3:4])[CH3:3].[CH:12](O)([CH3:14])[CH3:13].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[Br:1][C:2]([C@H:5]1[C@H:9]([O:10][CH:12]([CH3:14])[CH3:13])[O:8][C:7](=[O:11])[CH2:6]1)([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 6101p-Toluenesulfonic acidHCID 86739367HCID 86739367, compound

Product 1

HCID 86739368HCID 86739368, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 1.95 g of dl trans 4-(2-bromo-prop-2-yl)-5-hydroxy-tetrahydrofuran-2-one, 2 ml of isopropanol, 100 mg of p-toluene sulfonic acid and 30 ml of benzene was stirred at room temperature for 60 hours and was then washed with aqueous sodium bicarbonate solution. The mixture was extracted with benzene and the organic phase was dried and evaporated to dryness under reduced pressure to obtain 2 g of dl trans 4-(2-bromo-prop-2-yl)-5-isopropyloxy-tetrahydrofuran-2-one as an oily product which was used as is for the next step.

Workup

  1. washwas then washed with aqueous sodium bicarbonate solution
  2. extractionThe mixture was extracted with benzene
  3. customthe organic phase was dried
  4. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-0c6d074bda374bf1ac9566888c34446c
Source dataset
uspto-grants-1985_02
Patent number
US04500720

Reaction notes

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