Sodium Hydroxide → (3,6-Dimethyl-1,2-phenylene)dimethanol

HRID 1879524Notes

Reaction equation

HRID 1879524 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]12O[C:14]([CH3:18])([CH:15]=[CH:16]1)[CH:13]1[CH:9]2[C:10](=O)[O:11][C:12]1=[O:19].[OH-].[Na+]>O1CCCC1>[OH:11][CH2:10][C:9]1[C:8]([CH3:7])=[CH:16][CH:15]=[C:14]([CH3:18])[C:13]=1[CH2:12][OH:19]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 2450364,7-Dimethyl-3a,4,7,7a-tetrahydro-4,7-epoxy-2-benzofuran-1,3-dioneHCID 21226445Aluminium lithium hydride

Product 1

HCID 13220177(3,6-Dimethyl-1,2-phenylene)dimethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-78 °C

Procedure

A 1 L 3-necked RBF is charged with a 1.0M lithium aluminium hydride solution in tetrahydrofuran (175 mL, 0.175 mol) and anhydrous tetrahydrofuran (100 mL) under nitrogen. The solution is cooled to −78° C. and a solution of 1,7-dimethyl-4,10-dioxa-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione 2 (12.3 g, 0.070 mol) in anhydrous tetrahydrofuran (150 mL) is added from a dropping funnel over a period of 30 minutes The reaction mixture is heated to reflux and stirred for 45 h. The reaction mixture is cooled to 0° C. using an ice bath and 2M sodium hydroxide solution (20 mL) is slowly added dropwise. The mixture is allowed to warm up to 22° C. and the precipitate is filtered off and washed thoroughly with diethyl ether and tetrahydrofuran. The filtrate is concentrated in vacuo.

Workup

  1. temperatureis heated
  2. temperatureto reflux
  3. temperatureThe reaction mixture is cooled to 0° C.
  4. temperatureto warm up to 22° C.
  5. filtrationthe precipitate is filtered off
  6. washwashed thoroughly with diethyl ether and tetrahydrofuran
  7. concentrationThe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-22aaf414b26e4469b64d6b50aa33e9c9
Source dataset
uspto-grants-2012_11
Patent number
US08318048B2

Reaction notes

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