Water → HCID 58210237, compound

HRID 2390608Notes

Reaction equation

HRID 2390608 reaction equation
[C:1]1([CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][CH:14]([C:20](OCC)=[O:21])[C:15](OCC)=[O:16])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[OH-].[Na+]>C1(C)C=CC=CC=1.C1COCC1>[C:1]1([CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][CH:14]([CH2:15][OH:16])[CH2:20][OH:21])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 962Water2×HCID 14798Sodium HydroxideHCID 58210231HCID 58210231, compound

Product 1

HCID 58210237HCID 58210237, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

C6H5—CH2O—CH2CH2OCH2CH2—CH(COOC2H5)2 (5 g) from Step B was dissolved in 200 ml of toluene and 29.5 ml of LiA1H4 (1 M in THF) was added at 0-5° C. After stirring overnight at room temperature, 1 ml of water was added followed by 1.0 ml of 15% NaOH and 3.0 ml of water. The insoluble material was filtered and the filtrate was evaporated to dryness. The product was purified by flash chromatography on a silica gel column eluted with ethyl acetate. Combined fractions were evaporated to dryness. The final product was dried under vacuum overnight.

Workup

  1. filtrationThe insoluble material was filtered
  2. customthe filtrate was evaporated to dryness
  3. customThe product was purified by flash chromatography on a silica gel column
  4. washeluted with ethyl acetate
  5. customCombined fractions were evaporated to dryness
  6. dry with materialThe final product was dried under vacuum overnight

Sources & evidence

ORD record
ord-06836679b8f04ed1a3d469b2e76a18e2
Source dataset
uspto-grants-2012_09
Patent number
US08273833B2

Reaction notes

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