Benzoic Acid → 3-Ethoxy-2,4-dioxa-bicyclo[3,2,0]heptane

HRID 1413977Notes

Reaction equation

HRID 1413977 reaction equation
[CH2:1]([O:3][CH:4]([OH:6])[OH:5])[CH3:2].C(O)(=O)[C:8]1[CH:13]=[CH:12][CH:11]=CC=1>>[CH2:1]([O:3][CH:4]1[O:6][CH:12]2[CH:11]([CH2:8][CH2:13]2)[O:5]1)[CH3:2]

Participants

3

Reactant 2

HCID 243Benzoic AcidHCID 5231668Orthoameisensaureathylester

Product 1

HCID 202893363-Ethoxy-2,4-dioxa-bicyclo[3,2,0]heptaneYield 1,013.7%

Procedure

130.8 g (1.5 mols) of cyclobutane-cis-1,2-diol, 222.6 g (1.5 mols) of orthoformic acid ethyl ester and 15.0 g of benzoic acid are heated from 90° to 120° C. in the course of 3 hours. The ethanol which forms is distilled off continuously. Fractional distillation in vacuo gives 179.5 g (83%) of 3-ethoxy-2,4-dioxa-bicyclo[3,2,0]heptane (stereoisomer mixture), boiling point11 63°.

Workup

  1. distillationThe ethanol which forms is distilled off continuously
  2. distillationFractional distillation in vacuo

Sources & evidence

ORD record
ord-6204157f7e9142c19291ae2069e12e2c
Source dataset
uspto-grants-1981_02
Patent number
US04252738

Reaction notes

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