Water → (8-Methyl-1,4-dioxaspiro(4.5)decan-8-yl)methanol

HRID 1462923Notes

Reaction equation

HRID 1462923 reaction equation
[CH2:1]1[CH2:15][O:14][C:3]2([CH2:8][CH2:7][C:6]([CH3:13])([C:9](OC)=[O:10])[CH2:5][CH2:4]2)[O:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].C(OCC)(=O)C.O>CCOCC>[CH2:15]1[CH2:1][O:2][C:3]2([CH2:4][CH2:5][C:6]([CH3:13])([CH2:9][OH:10])[CH2:7][CH2:8]2)[O:14]1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 22591390Methyl 8-methyl-1,4-dioxaspiro[4.5]decane-8-carboxylate

Product 1

HCID 12568263(8-Methyl-1,4-dioxaspiro(4.5)decan-8-yl)methanolYield 89.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

The thus-obtained methyl 4,4-ethylenedioxy-1-methylcyclohexanecarboxylate (37.8 g) was dissolved in ether (100 ml), and the solution was added dropwise to a refluxing suspension of LiAlH4 (6.7 g) in ether (400 ml). After the addition, the mixture was stirred at room temperature for an hour and then cooled with ice. Ethyl acetate (20 ml) and then water (35 ml) were added dropwise cautiously thereto. The solid precipitate was filtered off, and the filtrate was distilled under reduced pressure to give 4,4-ethylenedioxy-1-methylcyclohexanemethanol (29.5 g, 89.9% yield, b.p. 120°-125° C./0.5 mmHg, m.p. 42°-43° C.).

Workup

  1. additionAfter the addition
  2. temperaturecooled with ice
  3. filtrationThe solid precipitate was filtered off
  4. distillationthe filtrate was distilled under reduced pressure

Sources & evidence

ORD record
ord-6dd396102f7743449c6ca1724ade3805
Source dataset
uspto-grants-1984_07
Patent number
US04461902

Reaction notes

Loading…