Water → Naphthalan

HRID 1623038Notes

Reaction equation

HRID 1623038 reaction equation
O[CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[C:11]([CH2:13][OH:14])=[CH:10][CH:9]=[CH:8]2.P(=O)(O)(O)O.O>C(Cl)Cl>[CH2:2]1[C:3]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][C:11]=3[CH2:13][O:14]1)[CH:6]=[CH:5][CH:4]=2

Participants

5

Reactant 3

HCID 962WaterHCID 1004Phosphoric AcidHCID 748461,8-Naphthalenedimethanol

Product 1

HCID 588214Naphthalan

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
140 °C

Procedure

A 1-L 3-neck flask equipped with an overhead stirrer, a condenser, and a thermocouple was charged with (8-hydroxymethyl-naphthalen-1-yl)-methanol (33.0 g, 0.175 mol), concentrated phosphoric acid (225 mL), and water (5 mL). The reaction mixture was stirred at 140° C. for 3 h, cooled to room temperature, diluted with CH2Cl2 (800 mL) and transferred to a 2-L separatory funnel. After washing the organic layer with water and saturated NaHCO3 it was dried over MgSO4 and evaporated to yield 1H,3H-Benzo[de]isochromene as a solid.

Workup

  1. customA 1-L 3-neck flask equipped with an overhead stirrer, a condenser
  2. temperaturecooled to room temperature
  3. customtransferred to a 2-L separatory funnel
  4. washAfter washing the organic layer with water and saturated NaHCO3 it
  5. dry with materialwas dried over MgSO4
  6. customevaporated

Sources & evidence

ORD record
ord-9ee44312a24b43fc8a9f7ed9d79926a9
Source dataset
uspto-grants-2014_07
Patent number
US08778956B2

Reaction notes

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