Hydrochloric Acid → 2,6-Dimethyl-4-(pyrrolidin-1-ylmethyl)phenol

HRID 1159422Notes

Reaction equation

HRID 1159422 reaction equation
[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[NH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1.[CH3:20][C:21]1[CH:22]=[C:23]([CH:26]=[C:27]([CH3:30])[C:28]=1[OH:29])[CH:24]=O.Cl>C(Cl)Cl>[CH3:20][C:21]1[CH:22]=[C:23]([CH2:24][N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)[CH:26]=[C:27]([CH3:30])[C:28]=1[OH:29]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 31268PyrrolidineHCID 752223,5-Dimethyl-4-hydroxybenzaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 27743672,6-Dimethyl-4-(pyrrolidin-1-ylmethyl)phenolYield 82.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

NaB(OAc)3H (22.1 g, 0.104 mol) was added in portions for 15 min to a mixture of pyrrolidine (8.1 mL, 0.098 mol) and 3,5-dimethyl-4-hydroxybenzaldehyde (12.5 g, 0.083 mol) in CH2Cl2 (100 mL) under vigorous stirring and cooling with an ice bath in an atmosphere of argon Ar. The mixture was stirred for 20 h and cooled with an ice bath. Concentrated HCl (19 mL) was added. The organic layer was separated and discarded. The aqueous one was alkalized with 10 N NaOH to pH 9 (30 mL) and extracted with chloroform (2×100 mL). The combined extracts were dried with Na2SO4, and evaporated to give the title compound (14 g, 82%) was obtained as white crystals. LCMS-data: 206.1 and 207.1 (M+H)+ (calculated for C13H19NO 205.1). 1H NMR (400 MHz)-data (DMSO-d6, J, Hz): 7.99 (br s, 1H, OH); 6.80 (s, 2H, ArH); 3.36 (s, 2H, CH2); 2.32-2.41 (m, 4H, CH2CH2CH2CH2); 2.13 (s, 6H, (CH3)2); 1.61-1.70 (m, 4H, CH2CH2CH2CH2).

Workup

  1. temperaturecooling with an ice bath in an atmosphere of argon Ar
  2. stirringThe mixture was stirred for 20 h
  3. temperaturecooled with an ice bath
  4. customThe organic layer was separated
  5. extractionextracted with chloroform (2×100 mL)
  6. dry with materialThe combined extracts were dried with Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-7fa93d504bae41819318d532eda40fe5
Source dataset
uspto-grants-2010_10
Patent number
US07812040B2

Reaction notes

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