Ethanol → Ethyl 4-(4-(adamantan-1-yl)phenoxy)butanoate

HRID 258972Notes

Reaction equation

HRID 258972 reaction equation
[C:1]12([C:11]3[CH:23]=[CH:22][C:14]([O:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])=[CH:13][CH:12]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.S(=O)(=O)(O)O.[CH2:29](O)[CH3:30]>>[CH2:29]([O:20][C:19](=[O:21])[CH2:18][CH2:17][CH2:16][O:15][C:14]1[CH:13]=[CH:12][C:11]([C:1]23[CH2:2][CH:3]4[CH2:4][CH:5]([CH2:6][CH:7]([CH2:9]4)[CH2:8]2)[CH2:10]3)=[CH:23][CH:22]=1)[CH3:30]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 214251534-[4-(1-Adamantyl)-phenoxy]butyric acid

Product 1

HCID 54179703Ethyl 4-(4-(adamantan-1-yl)phenoxy)butanoate

Procedure

1 mol of 4-[4-(1-adamantyl)-phenoxy]-butyric acid is dissolved in excess ethanol and boiled, with addition of 3% of concentrated sulphuric acid, for 3 hours under reflux, with exclusion of moisture. The product is concentrated to half its volume and partitioned between methylene chloride and water. The organic phase is washed until neutral, dried with sodium sulphate and evaporated in vacuo to give 4-[4-(1-adamantyl)-phenoxy]-butyric acid ethyl ester of melting point 45°-46° C.

Workup

  1. temperatureunder reflux, with exclusion of moisture
  2. concentrationThe product is concentrated to half its volume
  3. custompartitioned between methylene chloride and water
  4. washThe organic phase is washed until neutral,
  5. dry with materialdried with sodium sulphate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-1788dd8935e64c558b46953c3d053d88
Source dataset
uspto-grants-1977_07
Patent number
US04035413

Reaction notes

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