Hydrochloric Acid → 1,4-Dioxaspiro(4.5)decan-8-ol

HRID 399106Notes

Reaction equation

HRID 399106 reaction equation
[B-].[Na+].[CH2:3]1[O:13][C:6]2([CH2:11][CH2:10][C:9](=[O:12])[CH2:8][CH2:7]2)[O:5][CH2:4]1.Cl>CO>[CH2:4]1[O:5][C:6]2([CH2:11][CH2:10][CH:9]([OH:12])[CH2:8][CH2:7]2)[O:13][CH2:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 22959485Vertellus

Product 1

HCID 5673521,4-Dioxaspiro(4.5)decan-8-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydrate (2.4 g, 64 mmol) was added in portions to a stirred ice cold solution of 1,4 cyclohexanedione monoethylene ketal 38 (20 g, 128 mmol) in 60 mL of methanol (Step 35). After addition was complete, 1N HCl was added to the solution dropwise until a pH of 8 was obtained and then the solvent was removed by roto-evaporation. The product 39 (16.8 g, 84%) showed a single spot on TLC (Rf=0.4, ethyl acetate/hexane 20:80 solvent system, visualization was with acidic vanillin ethanol solution) and was used without further purification. 1H NMR (CDCl3) δ1.6-1.9 (m, 8H, ring-CH2), 3.8 (m, 1H, CH--O), 4.0 (s, 4H, ketal-CH2), 5.3 (s, 1H, OH).

Workup

  1. additionAfter addition
  2. customwas obtained
  3. customthe solvent was removed by roto-evaporation
  4. customwas used without further purification

Sources & evidence

ORD record
ord-f7bb252431bb48619f23732c50a5aaa1
Source dataset
uspto-grants-1998_10
Patent number
US05817776

Reaction notes

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