Benzene → HCID 86737365, compound

HRID 1732272Notes

Reaction equation

HRID 1732272 reaction equation
[C:1]([O:4][CH:5]([CH2:25][CH2:26][C:27]([CH3:29])=[CH2:28])[CH:6]([CH3:24])[CH2:7][CH2:8][CH2:9][C:10]1([CH3:23])[CH:16]2[O:17][C:13]([CH2:18][C:19]([O:21][CH3:22])=[O:20])([CH2:14][CH2:15]2)[CH2:12][O:11]1)(=[O:3])[CH3:2].C1C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CCOCC>[C:1]([O:4][CH:5]([CH2:25][CH:26]=[C:27]([CH3:28])[CH3:29])[CH:6]([CH3:24])[CH2:7][CH2:8][CH2:9][C:10]1([CH3:23])[CH:16]2[O:17][C:13]([CH2:18][C:19]([O:21][CH3:22])=[O:20])([CH2:14][CH2:15]2)[CH2:12][O:11]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 241BenzeneHCID 521998p-Toluenesulfonic acid monohydrateHCID 86737366HCID 86737366, compound

Product 1

HCID 86737365HCID 86737365, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of methyl (1RS,4SR,5RS)-4-(5-acetoxy-4,8-dimethyl-8-nonenyl)-4-methyl-3,8-dioxabicyclo [3.2.1] octane-1-acetate (93 mg, 0.24 mM), benzene (6 ml) and p-toluenesulfonic acid monohydrate (1 crystal) is heated to 80° C. for sixteen hours under nitrogen. The resulting mixture is cooled to room temperature and treated with ether (100 ml). The organic phase is washed with 5% sodium bicarbonate solution (5 ml) and dried (sodium sulfate). The solvent is removed in vacuo to give methyl (1RS,4SR,5RS)-4-(5-acetoxy-4,8-dimethyl-7-nonenyl)-4-methyl-3,8-dioxabicyclo [3.2.1] octane-1-acetate (72 mg, 90%) as a colorless oil. This material is homogeneous by thin layer chromatography and is used directely in the next step.

Workup

  1. temperatureThe resulting mixture is cooled to room temperature
  2. washThe organic phase is washed with 5% sodium bicarbonate solution (5 ml)
  3. dry with materialdried (sodium sulfate)
  4. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-e40f6f2881dc4bb5a68a80b7892230c7
Source dataset
uspto-grants-1980_12
Patent number
US04237054

Reaction notes

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