Thiophenol → HCID 13533747, compound

HRID 1154060Notes

Reaction equation

HRID 1154060 reaction equation
[CH3:1][C:2]1([CH3:11])[C:4]2([CH2:9][CH2:8][C:7]([CH3:10])=[CH:6][CH2:5]2)[O:3]1.[H-].[Na+].[C:14]1([SH:20])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(O)CCCC>[CH3:10][C:7]1[CH2:8][CH2:9][C:4]([C:2]([CH3:11])([S:20][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH3:1])([OH:3])[CH2:5][CH:6]=1

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 24758Sodium hydrideHCID 1073031-Oxaspiro[2.5]oct-5-ene, 2,2,6-trimethyl-

Product 1

HCID 13533747HCID 13533747, compoundYield 52.7%

Reagents, catalysts & solvents 1

HCID 62761-PentanolSolvent

Procedure

To a stirred solution of 76 g of 2,2,6-trimethyl-1-oxaspiro(2.5)oct-5-ene in 300 ml of n-pentanol were added 2.0 g of 60% sodium hydride and 60 g of thiophenol. After 18 hours reflux, the mixture was vacuum concentrated at 90°-95° C. The residue was dissolved in methylene chloride and washed twice with 2N sodium hydroxide. The dried solution was Claisen-distilled to give 106 g of crude product, b.p. 120°-125° C. Recrystallization from 250 ml of hexane gave 69.1 g of the desired product, m.p. 73°-74° C.

Workup

  1. temperatureAfter 18 hours reflux
  2. concentrationconcentrated at 90°-95° C
  3. dissolutionThe residue was dissolved in methylene chloride
  4. washwashed twice with 2N sodium hydroxide
  5. distillationThe dried solution was Claisen-distilled
  6. customto give 106 g of crude product, b.p. 120°-125° C
  7. customRecrystallization from 250 ml of hexane

Sources & evidence

ORD record
ord-97368b5ee82c4b7781413f9a71d2c9fd
Source dataset
uspto-grants-1984_12
Patent number
US04487945

Reaction notes

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