p-Toluenesulfonic acid → HCID 54572592, compound

HRID 1087133Notes

Reaction equation

HRID 1087133 reaction equation
[OH:1][C:2]1[CH:14]=[CH:13][C:5]([CH:6]=[CH:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:4][CH:3]=1.[O:15]1[CH:20]=[CH:19][CH2:18][CH2:17][CH2:16]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[OH-].[Na+]>CCOCC>[O:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH:16]1[O:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]=[CH:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 14798Sodium HydroxideHCID 349172P-hydroxyl ethyl cinnaMate

Product 1

HCID 54572592HCID 54572592, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To 30 ml of anhydrous ether solution containing 5 g of ethyl 4-hydroxycinnamate was added 7.1 ml of dihydropyran and 50 mg of p-toluenesulfonic acid were added, the mixture was stirred at a room temperature for 2 hours, the reaction mixture was neutralized with 1%-sodium hydroxide solution, washed with water, and dried with anhydrous sodium sulfate. The solvent was removed by evaporation to yield 6.8 g of ethyl 4-(2-tetrahydropyranyloxy)cinnamate. Colorless indefinite form crystals. Melting point: 52°-53° C.

Workup

  1. additionwere added
  2. washwashed with water
  3. dry with materialdried with anhydrous sodium sulfate
  4. customThe solvent was removed by evaporation

Sources & evidence

ORD record
ord-acd24d544e00498d9ef2e75d32a61a10
Source dataset
uspto-grants-1991_07
Patent number
US05034395

Reaction notes

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