Methyl Benzoate → HCID 19877240, compound

HRID 2106989Notes

Reaction equation

HRID 2106989 reaction equation
[CH2:1]([C:3]1([CH2:26][OH:27])[CH2:8][O:7][C:6]2([CH2:13][CH:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[S:11][CH:10]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:9]2)[O:5][CH2:4]1)[CH3:2].[C:28](OC)(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C1(C)C(C)=CC=CC=1>[CH2:1]([C:3]1([CH2:26][O:27][C:28](=[O:35])[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:4][O:5][C:6]2([CH2:9][CH:10]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[S:11][CH:12]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:13]2)[O:7][CH2:8]1)[CH3:2]

Participants

4

Reactant 2

HCID 7150Methyl BenzoateHCID 19877247(3-Ethyl-8,10-diphenyl-1,5-dioxa-9-thiaspiro[5.5]undecan-3-yl)methanol

Product 1

HCID 19877240HCID 19877240, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

19.2 g of 3-ethyl-3-hydroxymethyl-8,10-diphenyl-1,5-dioxa-9-thiaspiro[5.5]-undecane and 6.8 g of methyl benzoate are dissolved in 100 ml of xylene. About 20 ml of xylene are distilled off under a weak stream of nitrogen. After cooling to 110°, 0.1 g of LiNH2 are added and the mixture is heated at 135° for 8 hours, with stirring, the methanol formed being continuously distilled off together with a little xylene. After cooling to room temperature, 0.25 ml of glacial acetic acid and 3 g of bleaching earth are added. After stirring for 15 minutes, the mixture is filtered. The filtrate is filtered over 100 g of silica gel and evaporated in vacuo. The oily residue is dried at 70° in vacuo. 3-Ethyl-3-benzoyloxymethyl-8,10-diphenyl-1,5-dioxa-9-thiaspiro[5.5]-undecane is obtained as a pale yellowish resin.

Workup

  1. distillationAbout 20 ml of xylene are distilled off under a weak stream of nitrogen
  2. temperatureAfter cooling to 110°
  3. addition0.1 g of LiNH2 are added
  4. temperaturethe mixture is heated at 135° for 8 hours
  5. customthe methanol formed
  6. distillationbeing continuously distilled off together with a little xylene
  7. addition0.25 ml of glacial acetic acid and 3 g of bleaching earth are added
  8. stirringAfter stirring for 15 minutes
  9. filtrationthe mixture is filtered
  10. filtrationThe filtrate is filtered over 100 g of silica gel
  11. customevaporated in vacuo
  12. customThe oily residue is dried at 70° in vacuo

Sources & evidence

ORD record
ord-8aa910980a4d4737b1b0efe00adf5ad0
Source dataset
uspto-grants-1990_06
Patent number
US04933271

Reaction notes

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