Hydrochloric Acid → 2-(10-Hydroxydecyl)-5,6-dimethoxy-3-methylphenol

HRID 1905345Notes

Reaction equation

HRID 1905345 reaction equation
[OH:1][C:2]1[C:7]([O:8][CH3:9])=[C:6]([O:10][CH3:11])[CH:5]=[C:4]([CH3:12])[C:3]=1[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22](OC)=[O:23].[BH4-].[Na+].[Cl-].[Al+3].[Cl-].[Cl-].Cl>O1CCCC1.O>[OH:1][C:2]1[C:7]([O:8][CH3:9])=[C:6]([O:10][CH3:11])[CH:5]=[C:4]([CH3:12])[C:3]=1[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][OH:23]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 6451240Aluminum(III) ChlorideHCID 12824095Methyl 10-(2-hydroxy-3,4-dimethoxy-6-methylphenyl)decanoate

Product 1

HCID 128241262-(10-Hydroxydecyl)-5,6-dimethoxy-3-methylphenolYield 99.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
15 °C

Procedure

In tetrahydrofuran (1.8 l) was dissolved methyl 10-(2-hydroxy-3,4-dimethoxy-6-methylphenyl)decanoate (881 g, 2.5 mol.). To the solution was added a suspension of sodium borohydride (340 g, 9 mol.) in tetrahydrofuran (10.7 l), and the mixture was stirred. To the resulting suspension was added water (75 ml, 4.16 mol.). Aluminum chloride (400 g, 3 mol.) was dissolved in tetrahydrofuran (6.0 l). The solution was added dropwise to the above-mentioned suspension at a given rate in the course of 90 minutes, during which period the inner temperature of the reaction mixture was kept at 25±2° C. Then, the reaction mixture was stirred at the same temperature for further 30 minutes, which was then cooled to about 15° C. To the reaction mixture was added water (22 l) dropwise to cause decomposition, to which was then added dropwise hydrochloric acid (2.7 l). The mixture was subjected to extraction twice with 9 l each portion of toluene. Then, the toluene layers were combined and washed with a 5% aqueous solution of sodium hydrogen carbonate (4.4 l), followed by further washing with water (4.4 ). The toluene layer was concentrated under reduced pressure to obtain 10-(2-hydroxy-3,4-dimethoxy-6-methylphenyl)decan-1-ol (805 g, 2.48 mol., yield 99.2%) as an oily product.

Workup

  1. additionTo the solution was added
  2. additionThe solution was added dropwise to the above-mentioned suspension at a given rate in the course of 90 minutes, during which period the inner temperature of the reaction mixture
  3. customwas kept at 25±2° C
  4. stirringThen, the reaction mixture was stirred at the same temperature for further 30 minutes
  5. extractionThe mixture was subjected to extraction twice with 9 l each portion of toluene
  6. washwashed with a 5% aqueous solution of sodium hydrogen carbonate (4.4 l)
  7. washby further washing with water (4.4 )
  8. concentrationThe toluene layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d602823a13b343d08c7c5a9c65ed62e7
Source dataset
uspto-grants-1989_06
Patent number
US04842775

Reaction notes

Loading…