Hydrochloric Acid → HCID 19972803, compound

HRID 2259886Notes

Reaction equation

HRID 2259886 reaction equation
[C:1](Cl)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[OH:8][C:9]1[C:19]([C:20](=[O:23])[CH2:21][CH3:22])=[CH:18][CH:17]=[CH:16][C:10]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12].Cl>N1C=CC=CC=1>[C:1]([O:8][C:9]1[C:19]([C:20](=[O:23])[CH2:21][CH3:22])=[CH:18][CH:17]=[CH:16][C:10]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 62493Pivaloyl chlorideHCID 10944050HCID 10944050, compound

Product 1

HCID 19972803HCID 19972803, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

6 ml of pivaloyl chloride was added dropwise into a stirred solution of 8.9 g of ethyl 2-hydroxy-3-propionylbenzoate in 20 ml of anhydrous pyridine. The reaction mixture was stirred at 80° C. for 6 hours, cooled at room temperature and poured into a mixture of 200 g of crushed ice and 30 ml of 10N aqueous hydrochloric acid solution. After extraction with diethyl ether, the organic phase was washed with brine, dried on anhydrous sodium sulfate and evaporated to dryness in vacuo, yielding 11.4 g of crude ethyl 2-pivaloyloxy-3-propionylbenzoate.

Workup

  1. temperaturecooled at room temperature
  2. extractionAfter extraction with diethyl ether
  3. washthe organic phase was washed with brine
  4. dry with materialdried on anhydrous sodium sulfate
  5. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-4cd45b3acafe47f9a2f86ff85d485418
Source dataset
uspto-grants-1995_12
Patent number
US05474994

Reaction notes

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