Ethanol → HCID 14578963, compound

HRID 1679238Notes

Reaction equation

HRID 1679238 reaction equation
S(=O)(=O)(O)O.S([O-])([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]CCCCCC)(=O)=O.[Na+].[C:24](=[O:27])([O-])[O-:25].[Na+].[Na+].[CH2:30](O)[CH3:31]>S(=O)(=O)(O)O.C1C=CC=CC=1>[OH:9][CH2:10][C:11]#[C:12][CH2:13][CH2:14][CH2:15][C:24]([O:25][CH2:30][CH3:31])=[O:27]

Participants

7

Reactant 4

HCID 702Ethanol2×HCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 3423265Sodium Lauryl Sulfate

Product 1

HCID 14578963HCID 14578963, compound

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 241BenzeneSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 20 g of 7-(α-tetrahydropyranyloxy)-5-heptynoic acid, 12 g of ethanol, 50 cc of benzene and 2 drops of concentrated sulfuric acid was refluxed under nitrogen for 3 hours and after letting the mixture return to room temperature, 20 cc of 12.5% sulfuric acid, 30 cc of ethanol and traces of sodium lauryl sulfate were added thereto. The mixture was stirred overnight at 20° C and was then neutralized with sodium carbonate. The mixture was extracted with ether and the ether extracts were dried and the solvent was evaporated off under reduced pressure. The residue was rectified to obtain 8.5 g of ethyl 7-hydroxy-5-heptynoate identical of that of Step E of Example I.

Workup

  1. temperaturewas refluxed under nitrogen for 3 hours
  2. customto room temperature
  3. extractionThe mixture was extracted with ether
  4. dry with materialthe ether extracts were dried
  5. customthe solvent was evaporated off under reduced pressure

Sources & evidence

ORD record
ord-efbd42af3f804cfabd726de69cf0e734
Source dataset
uspto-grants-1978_03
Patent number
USRE029587

Reaction notes

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