Sulfuric Acid → HCID 19857607, compound

HRID 1605810Notes

Reaction equation

HRID 1605810 reaction equation
[H-].C([Al+]C[CH:8]([CH3:10])C)C(C)C.C(C[C:17]1([OH:27])[CH2:26][CH2:25][CH:24]2[CH:19]([CH2:20][CH2:21][CH2:22][CH2:23]2)[CH2:18]1)(OCC)=O.S(=O)(=O)(O)[OH:29]>C1C=CC=CC=1>[OH:29][CH2:8][CH2:10][CH:18]1[CH:19]2[CH:24]([CH2:23][CH2:22][CH2:21][CH2:20]2)[CH2:25][CH2:26][CH:17]1[OH:27]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 21225700DiisobutylaluminumhydrideHCID 54395777HCID 54395777, compound

Product 1

HCID 19857607HCID 19857607, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A solution of 235 g of diisobutyl aluminium hydride in 300 ml of anhydrous benzene is added dropwise to a mixture of 120 g of 2-carbethoxymethyl-2-hydroxy-decalin and 120 ml of anhydrous benzene under nitrogen. During the addition the temperature of the reaction mass is held between 15° and 20°C. This temperature is maintained for a further two hours after the end of the addition. The mass is then cooled to 0°C and hydrolysed with 1500 ml of a 10% aqueous solution of sulphuric acid. The temperature is allowed to return to ambient, the organic layer decanted and the mother liquor extracted twice with 250 ml of benzene. The benzene extracts are then combined and washed to neutrality. After distillation of the solvent on a water bath under reduced pressure the crude product is rectified giving 72 g of 2-hydroxy-ethyl-2-hydroxy-decalin (72% yield) having b.p.1 = 147°.

Workup

  1. additionDuring the addition the temperature of the reaction mass
  2. customis held between 15° and 20°C
  3. temperatureThis temperature is maintained for a further two hours
  4. additionafter the end of the addition
  5. customthe organic layer decanted
  6. extractionthe mother liquor extracted twice with 250 ml of benzene
  7. washwashed to neutrality
  8. distillationAfter distillation of the solvent on a water bath under reduced pressure the crude product

Sources & evidence

ORD record
ord-b0569e167a064a4e83759c41d45077b7
Source dataset
uspto-grants-1976_04
Patent number
US03951875

Reaction notes

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