Ammonium Chloride → HCID 68121721, compound

HRID 2072449Notes

Reaction equation

HRID 2072449 reaction equation
OC([CH2:4][C:5]([CH3:15])([CH3:14])[C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:7])C.C[C:17](C)(C)[C:18]1(CC(C2C=CC=CC=2)=O)OCC[O:19]1.[H-].C[O:36][CH2:37][CH2:38]O[Al+]OCCOC.[Na+].[H-].[Cl-].[NH4+]>C1C=CC=CC=1.O1CCCC1>[CH3:15][C:5]([CH3:4])([CH3:14])[C:6]1([C:8]2[CH:9]=[CH:10][C:11]([CH:37]([OH:36])[CH3:38])=[CH:12][CH:13]=2)[O:7][CH2:17][CH2:18][O:19]1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 14491690HCID 14491690, compoundHCID 21409411HCID 21409411, compoundHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydride

Product 1

HCID 68121721HCID 68121721, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3.0 grams of 4 (2,2-dimethyl-1,1-ethylenedioxypropyl)-acetophenone in 150 ml. tetrahydrofuran is placed in a 250 ml. flask fitted with a dropping funnel and a magnetic stirring bar. Ten milliliters of a 70% solution of sodium bis-(2-methoxyethoxy)-aluminum hydride in benzene is placed in the dropping funnel. The solution is added over 30 minutes, and after the addition is complete, the mixture is stirred for 30 minutes, following which it is poured onto 100 grams of crushed ice to which 50 ml. of saturated ammonium chloride solution has been added. The organic phase is separated and the aqueous phase is extracted thrice with chloroform. The extracts are added to the organic phase, and the combined organic material is dried over anhydrous potassium carbonate. The drying agent is filtered off and the solvent is removed from the filtrate under reduced pressure on a rotary evaporator. The resulting oil is purified by column chromatography using silica gel as the support and benzene as the eluant to give 4-(2,2-dimethyl-1,1-ethylenedioxypropyl)-α-methylbenzyl alcohol, (m.p. 67°-70° C.)

Workup

  1. customflask fitted with a dropping funnel and a magnetic stirring bar
  2. additionThe solution is added over 30 minutes
  3. additionafter the addition
  4. customThe organic phase is separated
  5. extractionthe aqueous phase is extracted thrice with chloroform
  6. additionThe extracts are added to the organic phase
  7. dry with materialthe combined organic material is dried over anhydrous potassium carbonate
  8. filtrationThe drying agent is filtered off
  9. customthe solvent is removed from the filtrate under reduced pressure on a rotary evaporator
  10. customThe resulting oil is purified by column chromatography

Sources & evidence

ORD record
ord-d22c0bc305aa45d8a6dfd359f1e5b587
Source dataset
uspto-grants-1977_09
Patent number
US04051261

Reaction notes

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