Ethanol → Ethyl 2-[4-(4-chlorophenyl)benzyloxy]-2-phenylacetate

HRID 1105873Notes

Reaction equation

HRID 1105873 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:25]=[CH:24][C:11]([CH2:12][O:13][CH:14]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:15]([OH:17])=[O:16])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.S(=O)(=O)(O)O.C(=O)(O)[O-].[CH2:35](O)[CH3:36]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:25]=[CH:24][C:11]([CH2:12][O:13][CH:14]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:15]([O:17][CH2:35][CH3:36])=[O:16])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 769Bicarbonate IonHCID 1118Sulfuric AcidHCID 98633512-[4-(4-Chlorophenyl)benzyloxy]-2-phenylacetic acid

Product 1

HCID 20555293Ethyl 2-[4-(4-chlorophenyl)benzyloxy]-2-phenylacetate

Procedure

A solution of 2-[4-(4-chlorophenyl)benzyloxy]-2-phenylacetic acid (8.0 g.) in ethanol (200 ml.) containing concentrated sulphuric acid (1 ml.) was heated under reflux for 90 minutes, then cooled to room temperature, and carefully neutralised by addition of an excess of saturated aqueous bicarbonate solution. The mixture obtained was evaporated and the residue extracted thoroughly with ethyl acetate. The combined extracts were washed with water, dried (MgSO4) and evaporated to give ethyl 2-[4-(4-chlorophenyl)benzyloxy]-2-phenylacetate (6.65 g.), m.p. 50°-51° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 90 minutes
  3. customThe mixture obtained
  4. customwas evaporated
  5. extractionthe residue extracted thoroughly with ethyl acetate
  6. washThe combined extracts were washed with water
  7. dry with materialdried (MgSO4)
  8. customevaporated

Sources & evidence

ORD record
ord-849d0e41554c4a528911e78e602a55cf
Source dataset
uspto-grants-1982_01
Patent number
US04310544

Reaction notes

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