Water → HCID 59864392, compound

HRID 1093936Notes

Reaction equation

HRID 1093936 reaction equation
[C:1]1([OH:13])[CH:12]=[C:6]([CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[CH:5]=[C:3]([OH:4])[CH:2]=1.O=[C:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH:16]1[C:21](OCC)=[O:22].P(Cl)(Cl)(Cl)=O.O>C1(C)C=CC=CC=1>[OH:13][C:1]1[CH:12]=[C:6]([CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[CH:5]=[C:3]2[C:2]=1[C:15]1[CH2:20][CH2:19][CH2:18][CH2:17][C:16]=1[C:21](=[O:22])[O:4]2

Participants

6

Reactant 4

HCID 962WaterHCID 10377OlivetolHCID 24813Phosphorus oxychlorideHCID 95543Ethyl 2-oxocyclohexanecarboxylate

Product 1

HCID 59864392HCID 59864392, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Olivetol (49.5 g, 261 mmol) and ethyl 2-oxocyclohexanecarboxylate (47.7 ml, 285 mmol) were initially introduced in toluene and, after addition of 28.8 ml (310 mmol) of phosphoryl chloride, were stirred at room temp. for 38 h. The reaction mixture was slowly poured into 400 ml of water and stirred vigorously for 30 min. The precipitated yellow solid was filtered off and washed with water and toluene. The pale-yellow solid was taken up in hot ethyl methyl ketone, washed with aqueous saturated sodium hydrogencarbonate soln. solution and sat. sodium chloride solution, dried over sodium sulfate, filtered and evaporated in vacuo. Crystallisation of the crude product from acetonitrile/toluene gave 32.7 g (82%) of 1-hydroxy-3-pentyl-7,8,9,10-tetra-hydrobenzo[c]chromen-6-one as colourless crystals.

Workup

  1. stirringstirred vigorously for 30 min
  2. filtrationThe precipitated yellow solid was filtered off
  3. washwashed with water and toluene
  4. washwashed with aqueous saturated sodium hydrogencarbonate soln
  5. dry with materialsolution and sat. sodium chloride solution, dried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customCrystallisation of the crude product from acetonitrile/toluene

Sources & evidence

ORD record
ord-06a44ba39def4a99ad9d87c2f1759615
Source dataset
uspto-grants-2012_03
Patent number
US08133887B2

Reaction notes

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