Sodium Hydroxide → (cis-3-Methoxymethoxycyclohexyl)methanol

HRID 854640Notes

Reaction equation

HRID 854640 reaction equation
[CH3:1][O:2][CH2:3][O:4][C@@H:5]1[CH2:10][CH2:9][CH2:8][C@H:7]([C:11](OC)=[O:12])[CH2:6]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+].[O-]S([O-])(=O)=O.[Mg+2]>C(OCC)C.C(OCC)(=O)C>[CH3:1][O:2][CH2:3][O:4][C@@H:5]1[CH2:10][CH2:9][CH2:8][C@H:7]([CH2:11][OH:12])[CH2:6]1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 21226445Aluminium lithium hydrideHCID 69240434Methyl cis-3-methoxymethoxycyclohexanecarboxylate

Product 1

HCID 69240471(cis-3-Methoxymethoxycyclohexyl)methanolYield 90.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

9.0 g of methyl cis-3-methoxymethoxycyclohexanecarboxylate are dissolved in 280 ml of diethyl ether, 2.2 g of LiAlH4 are added and the mixture is stirred at room temperature. After 4 h, at 0° C., 10 ml of ethyl acetate and then 15 ml of 10N NaOH are added dropwise. The suspension is stirred for 1 h, MgSO4 is added, the mixture is filtered through Celite and the filtrate is concentrated, giving 7.0 g of (cis-3-methoxymethoxycyclo-hexyl)methanol as a colorless oil. C9H18O3 (174), MS(ESI): 175 (MH+).

Workup

  1. stirringThe suspension is stirred for 1 h
  2. filtrationthe mixture is filtered through Celite
  3. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-54c0286b70de41eba438c2483540c26f
Source dataset
uspto-grants-2007_08
Patent number
US07259177B2

Reaction notes

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