Water → HCID 20315579, compound

HRID 2419358Notes

Reaction equation

HRID 2419358 reaction equation
[C:1]([C:4]1[CH:14]=[CH:13][C:7]([O:8][CH2:9][C:10]([OH:12])=[O:11])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[CH2:15](O)[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].S(=O)(=O)(O)O.O>C1C=CC=CC=1>[C:1]([C:4]1[CH:14]=[CH:13][C:7]([O:8][CH2:9][C:10]([O:12][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[O:11])=[CH:6][CH:5]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 81031-HexanolHCID 74655(p-Acetylphenoxy)acetic acid

Product 1

HCID 20315579HCID 20315579, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 4-acetylphenoxyacetic acid (20.0g.), n-hexanol (10.5g.) and concentrated sulphuric acid (2ml.) in benzene (100ml.) was heated under reflux for 6 hours using a water separator.cThe mixture was then evaporated and the residue dissolved in n-pentane (50ml.). The solution was washed with water (3 × 30ml.) sodium bicarbonate solution (1 × 50ml.) and water again (1 × 50ml.). The solution was evaporated and the residue chromatographed on alumina to give n-hexyl 4-acetylphenoxyacetate, I.R. peaks at 1760 and 1680 cm-1.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 6 hours
  3. customwas then evaporated
  4. dissolutionthe residue dissolved in n-pentane (50ml.)
  5. washThe solution was washed with water (3 × 30ml.) sodium bicarbonate solution (1 × 50ml.) and water again (1 × 50ml.)
  6. customThe solution was evaporated
  7. customthe residue chromatographed on alumina

Sources & evidence

ORD record
ord-31aab53d7b3045d792441eafc4b2b016
Source dataset
uspto-grants-1978_08
Patent number
US04105790

Reaction notes

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