Acetic Acid → HCID 19804848, compound

HRID 344776Notes

Reaction equation

HRID 344776 reaction equation
[CH2:1]([O:8][CH:9]1[CH2:14][CH2:13]C(C#N)[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[C:18]([OH:21])(=[O:20])[CH3:19]>>[CH2:1]([O:8][CH:9]1[CH2:14][CH2:13][CH:19]([C:18]([OH:21])=[O:20])[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 467807704-(Benzyloxy)cyclohexane-1-carbonitrile

Product 1

HCID 19804848HCID 19804848, compound

Procedure

The crude 4-benzyloxycyclohexane-1-nitrile (4.0 g) was refluxed with stirring with a mixture of glacial acetic acid (16 ml) and concentrated hydrochloric acid (24 ml) for 20 hours. The reaction mixture was cooled, the solid removed by filtration and washed with water. The product was ground with 2M sodium hydroxide solution (70 ml) and then diluted with water. Unchanged nitrile was removed by filtration and the filtrate acidified with concentrated hydrochloric acid. White crystals separated and were collected by filtration, washed with water and dried to yield 4-benzyloxycyclohexane-1-carboxylic acid m.p. 170°-180° C.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customthe solid removed by filtration
  3. washwashed with water
  4. additiondiluted with water
  5. customUnchanged nitrile was removed by filtration
  6. customWhite crystals separated
  7. filtrationwere collected by filtration
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-3aa3c5219a44421d8de6d73e59c11f0a
Source dataset
uspto-grants-1991_10
Patent number
US05053432

Reaction notes

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