Hydrochloric Acid → 2,6-Diethyl-4-methylbenzyl alcohol

HRID 1890229Notes

Reaction equation

HRID 1890229 reaction equation
[Mg].[CH2:2]([C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[C:6]([CH2:11][CH3:12])[C:5]=1Br)[CH3:3].[CH2:14]=[O:15].Cl>II.BrCCBr.O1CCCC1>[CH2:2]([C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[C:6]([CH2:11][CH3:12])[C:5]=1[CH2:14][OH:15])[CH3:3]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 5462224MagnesiumHCID 115794912-Bromo-1,3-diethyl-5-methylbenzene2×

Product 1

HCID 667075402,6-Diethyl-4-methylbenzyl alcohol

Reagents, catalysts & solvents 3

HCID 807IodineCatalyst2×HCID 78391,2-DibromoethaneCatalyst2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Under a nitrogen atmosphere, 11.24 g of magnesium, 200 g of tetrahydrofuran, 0.1 g of iodine and 1.0 g of 1,2-dibromoethane were mixed. This mixture was heated to 60° C. To this mixture, a small amount of 2,6-diethyl-4-methylbromobenzene was added. To this mixture, 0.1 g of iodine and 1.0 g of 1,2-dibromoethane were added. Then, 2,6-diethyl-4-methylbromobenzene (the total amount including the amount added first: 100.12 g) was added dropwise over 2.5 hours. After completion of addition, the resultant mixture was stirred at 50° C. for 1.5 hours. This mixture was cooled to 30° C. To this mixture, 14.84 g of paraformaldehyde was added portionwise in five additions over 30 minutes. The resultant mixture was stirred at 30° C. for 2 hours. To the reaction mixture, 143 g of 10% hydrochloric acid was added, followed by extraction with 300 g of tert-butyl methyl ether. The organic layer was dried over anhydrous magnesium sulfate and then concentrated to obtain 77.56 g of 2,6-diethyl-4-methylbenzyl alcohol as a yellow crystal.

Workup

  1. additionadded first
  2. addition100.12 g) was added dropwise over 2.5 hours
  3. additionAfter completion of addition
  4. temperatureThis mixture was cooled to 30° C
  5. extractionfollowed by extraction with 300 g of tert-butyl methyl ether
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4de7e374ef0a41a9ae9df773b21d48ae
Source dataset
uspto-grants-2013_08
Patent number
US08507410B2

Reaction notes

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