Ethanol → 4-(1,4-Dioxaspiro[4.5]dec-8-yl)-1,3-benzenediol

HRID 23600

Reaction equation

HRID 23600 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:16]2[CH2:25][CH2:24][C:19]3([O:23][CH2:22][CH2:21][O:20]3)[CH2:18][CH:17]=2)=[C:13]([OH:15])[CH:14]=1)C1C=CC=CC=1.O1CCCC1.C(O)C>ClCCl.[Pd]>[O:20]1[C:19]2([CH2:24][CH2:25][CH:16]([C:12]3[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][C:13]=3[OH:15])[CH2:17][CH2:18]2)[O:23][CH2:22][CH2:21]1

Participants

6

Reactant 3

HCID 702EthanolHCID 8028TetrahydrofuranHCID 117392405-(Benzyloxy)2-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)phenol

Product 1

HCID 99212574-(1,4-Dioxaspiro[4.5]dec-8-yl)-1,3-benzenediolYield 95.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolvent

Procedure

A flask equipped with magnetic stirrer was charged with 5-(benzyloxy)-2-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)phenol (14.5 g, 42.8 mmol) and tetrahydrofuran (50 ml) and ethanol (100 ml) and palladium (4.54 g, 10% on activated carbon) were added sequentially. The reaction vessel was then evacuated, placed under a hydrogen atmosphere and stirred vigorously for 24 hr. The reaction mixture was filtered through a celite plug, washing with ethyl acetate. The filtrate was concentrated in vacuo to give an off white solid. The crude solid was slurried in dichloromethane (200 ml), affording the title compound (10.2 g, 95%) as a white solid. m/z(ES+) 251(M+H+).

Workup

  1. customA flask equipped with magnetic stirrer
  2. additionwere added sequentially
  3. customThe reaction vessel was then evacuated
  4. filtrationThe reaction mixture was filtered through a celite plug
  5. washwashing with ethyl acetate
  6. concentrationThe filtrate was concentrated in vacuo
  7. customto give an off white solid

Sources & evidence

ORD record
ord-20dfcce9f0c546d8b9b04dcc962410fc
Source dataset
uspto-grants-2005_02
Patent number
US06852747B2

Linked notes

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