Ethanol → HCID 18347834, compound

HRID 1395689Notes

Reaction equation

HRID 1395689 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)[O:9][CH2:10][C:11]([O:13]CC)=[O:12])=[CH:4][CH:3]=1.[OH-].[Na+].C(O)C>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:16]2[CH:17]=[CH:18][C:19]([Cl:22])=[CH:20][CH:21]=2)[O:9][CH2:10][C:11]([OH:13])=[O:12])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 57188419HCID 57188419, compound

Product 1

HCID 18347834HCID 18347834, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of crude ethyl di-(4-chlorophenyl)methyloxyacetate (9 g.), sodium hydroxide (5 g.), ethanol (150 ml.) and water (5 ml.) was heated under reflux for 16 hours. The mixture was evaporated and the residue was diluted with water (100 ml.) and ether (30 ml.). The ether extracts were discarded and the aqueous phase was acidified to pH 2-3 with 20% v/v hydrochloric acid. The mixture was extracted with ether and the extracts were dried (MgSO4) and evaporated. The residual solid obtained was crystallised from a mixture of ethyl acetate and petrol to give di-(4-chlorophenyl)methyloxyacetic acid, m.p. 108°-110°, in 64% yield.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 16 hours
  3. customThe mixture was evaporated
  4. additionthe residue was diluted with water (100 ml.) and ether (30 ml.)
  5. extractionThe mixture was extracted with ether
  6. dry with materialthe extracts were dried (MgSO4)
  7. customevaporated
  8. customThe residual solid obtained
  9. customwas crystallised from a mixture of ethyl acetate and petrol

Sources & evidence

ORD record
ord-7168cc2ccef946f9b455fc1b5582941c
Source dataset
uspto-grants-1980_05
Patent number
US04205087

Reaction notes

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