Water → HCID 86734503, compound

HRID 436393Notes

Reaction equation

HRID 436393 reaction equation
C([CH:3]1[O:7][CH:6]([CH2:8][CH2:9][CH2:10][CH2:11][OH:12])[CH2:5][O:4]1)=C.[C:13](O)(=O)C=C.C1(C)C=CC(S(O)(=O)=O)=CC=1.[H][H].[OH2:31]>ClCCl.COCCOC>[CH2:9]([C:10](=[CH2:13])[C:11]([O-:12])=[O:31])[CH3:8].[OH:12][CH2:11][CH2:10][CH2:9][CH2:8][CH:6]1[CH2:5][O:4][CH2:3][O:7]1

Participants

8

Reactant 5

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 6581Acrylic AcidHCID 212169861,3-Dioxolane-4-butanol, 2-ethenyl-HCID 178418361HCID 178418361, compound

Product 1

HCID 86734503HCID 86734503, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 172.2 grams (1 mole) of 2-vinyl-4(4-hydroxybutyl)-1,3-dioxolane (Comonomer B herein), 72.1 grams (1 mole) of acrylic acid and 0.1 gram of p-toluenesulfonic acid in 5 ml. of 1,2-dimethoxyethane was heated for 10 hours at 50°-60° C. After adding water (150 ml) and dichloromethane (200 ml), the non aqueous layer was washed successively with 100 ml. of 5 per cent sodium bicarbonate and two 100-ml. portions of water, and was then dried over magnesium sulfate. Hydroquinone (0.5 gram) stabilizer was added, the magnesium sulfate removed by filtration and the solvent evaporated under reduced pressure. The resulting oil was distilled through a 6-inch Vigreaux column to give 46.2 grams (19 weight per cent yield) of colorless product having a boiling point of 83°-87° C. at 1 mm. pressure. Upon analysis, the product was found to contain 62.28and 9.12 weight per cent of carbon and hydrogen, respectively. The corresponding calculated values, based on the empirical formula, C12H20O5, are 59.00 and 8.25.

Workup

  1. washthe non aqueous layer was washed successively with 100 ml
  2. dry with materialportions of water, and was then dried over magnesium sulfate
  3. additionHydroquinone (0.5 gram) stabilizer was added
  4. customthe magnesium sulfate removed by filtration
  5. customthe solvent evaporated under reduced pressure
  6. distillationThe resulting oil was distilled through a 6-inch Vigreaux column
  7. customto give
  8. custom46.2 grams (19 weight per cent yield) of colorless product

Sources & evidence

ORD record
ord-95d1654a36c14790acc4d3b30ede36b1
Source dataset
uspto-grants-1977_02
Patent number
US04009129

Reaction notes

Loading…