Sodium Chloride → 4,4-Dimethyl-6-(1-hydroxyethyl)chroman

HRID 1382909

Reaction equation

HRID 1382909 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[O:10][CH2:9][CH2:8][C:7]2([CH3:15])[CH3:14])(=[O:3])[CH3:2].[BH4-].[Na+].[Cl-].[Na+]>CO>[CH3:15][C:7]1([CH3:14])[C:6]2[C:11](=[CH:12][CH:13]=[C:4]([CH:1]([OH:3])[CH3:2])[CH:5]=2)[O:10][CH2:9][CH2:8]1

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 4311764Sodium borohydrideHCID 134781601-(4,4-Dimethyl-3,4-dihydro-2H-1-benzopyran-6-yl)ethan-1-one

Product 1

HCID 140102484,4-Dimethyl-6-(1-hydroxyethyl)chromanYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 6.0 g of 6-acetyl-4,4-dimethylchroman in 50 ml of methanol was added, all in one portion, with stirring, 3.78 g of sodium borohydride at ca. 0° C. Stirring was continued at ca. 0° C. for 1.5 hours, and then the reaction mixture was poured into 500 ml of saturated sodium chloride solution. The resulting mixture was extracted with diethyl ether, and the combined ether extracts were dried (MgSO4) and evaporated in vacuo to give 6.0 g of the title compound as an oil.

Workup

  1. customat ca. 0° C
  2. stirringStirring
  3. extractionThe resulting mixture was extracted with diethyl ether
  4. dry with materialthe combined ether extracts were dried (MgSO4)
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-752af348fc5e4b3c8d6b1a3553a906ad
Source dataset
uspto-grants-1989_02
Patent number
US04808597

Linked notes

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