Sodium Hydroxide → HCID 14476076, compound

HRID 1904311Notes

Reaction equation

HRID 1904311 reaction equation
[CH3:1][S:2]([C:5]1[CH:21]=[CH:20][C:8]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH2:16][C:17]([OH:19])=O)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[OH-].[Na+]>>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]2[O:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[CH2:16][C:17](=[O:19])[C:20]=2[CH:21]=1)(=[O:3])=[O:4]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 12245876HCID 12245876, compound

Product 1

HCID 14476076HCID 14476076, compound

Procedure

A mixture of 1.0 g of 2-(4-methylsulfonylphenoxy)phenylacetic acid and 10 ml of polyphosophoric acid under nitrogen is stirred at 90°-100° C. for 2 hours. The reaction mixture is permitted to cool and then poured into 100 ml of an ice-water slurry. The aqueous solution is basified with 20% sodium hydroxide before being extracted with methylene chloride. The combined extracts are dried and then evaporated to dryness leaving an oil. The oil is chromatographed through a silica gel/methylene chloride column with 2% methanol in methylene chloride. The chromatographed solution is evaporated to dryness leaving an oil which solidifies on standing. The solid is triturated with pentane to provide 10,11-dihydro-2-methylsulfonyl-11-oxodibenz[b,f]oxepin, mp 105°-106° C.

Workup

  1. temperatureto cool
  2. extractionbefore being extracted with methylene chloride
  3. customThe combined extracts are dried
  4. customevaporated to dryness
  5. customleaving an oil
  6. customThe oil is chromatographed through a silica gel/methylene chloride column with 2% methanol in methylene chloride
  7. customThe chromatographed solution is evaporated to dryness
  8. customleaving an oil which
  9. customThe solid is triturated with pentane

Sources & evidence

ORD record
ord-61a004345523420d9e24b1bd4bd3289c
Source dataset
uspto-grants-1989_06
Patent number
US04837227

Reaction notes

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