Benzyl Chloride → HCID 14676204, compound

HRID 1638816Notes

Reaction equation

HRID 1638816 reaction equation
[OH:1][C:2]1[C:3]([OH:14])=[CH:4][C:5]2[C:11](=[O:12])[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:13]=1.[CH2:15](Cl)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:15]([O:1][C:2]1[C:3]([OH:14])=[CH:4][C:5]2[C:11](=[O:12])[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:13]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 277845MLS002919905

Product 1

HCID 14676204HCID 14676204, compoundYield 59.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2,3-dihydroxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-one (10 g), benzyl chloride (8 g), anhydrous potassium carbonate (9 g) and acetone (200 ml) is stirred at 50° C. for two hours. The reaction mixture is cooled and filtered off. The filtrate is concentrated under reduced pressure. The concentrate is dissolved in ethyl acetate. The organic layer is washed with water, dried and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (eluent, hexane:ethyl acetate:methylene chloride=3:1:1) to afford 2-benzyloxy-3-hydroxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-one (8.8 g). This product is recrystallized from ethyl acetate-hexane to give colorless needles, m.p. 127°-128° C.

Workup

  1. temperatureThe reaction mixture is cooled
  2. filtrationfiltered off
  3. concentrationThe filtrate is concentrated under reduced pressure
  4. dissolutionThe concentrate is dissolved in ethyl acetate
  5. washThe organic layer is washed with water
  6. customdried
  7. concentrationconcentrated under reduced pressure
  8. customThe residue is purified by silica gel column chromatography (eluent, hexane:ethyl acetate:methylene chloride=3:1:1)

Sources & evidence

ORD record
ord-d5d2d056c3fc49aab4bdd77239e26310
Source dataset
uspto-grants-1989_11
Patent number
US04880809

Reaction notes

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