Hydrochloric Acid → Methyl (2-(hydroxymethyl)-3-methylphenyl)carbamate

HRID 1762196Notes

Reaction equation

HRID 1762196 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].[NH2:6][C:7]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[C:8]=1[CH2:9][OH:10].N1C=CC=CC=1.Cl>C(Cl)Cl>[CH3:5][O:4][C:2]([NH:6][C:7]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[C:8]=1[CH2:9][OH:10])=[O:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 6586Methyl chloroformateHCID 15339417(2-Amino-6-methylphenyl)methanol

Product 1

HCID 14368454Methyl (2-(hydroxymethyl)-3-methylphenyl)carbamateYield 81.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of methyl chloroformate (0.416 g) in methylene chloride (1 ml) was added dropwise to a solution of 2-amino-6-methylbenzyl alcohol (0.549 g) and pyridine (0.364 g) in methylene chloride (10 ml) with ice cooling. After being stirred for 1 hour, the mixture was poured into 1N hydrochloric acid and extracted with methylene chloride. The extract was washed with water, dried over magnesium sulfate, and evaporated in vacuo. The crystalline residue was washed with n-hexane and dried to give 2-methoxycarbonylamino-6-methylbenzyl alcohol (0.64 g).

Workup

  1. extractionextracted with methylene chloride
  2. washThe extract was washed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. washThe crystalline residue was washed with n-hexane
  6. customdried

Sources & evidence

ORD record
ord-93fddaa1c6c34e838745634ddd0d0d8a
Source dataset
uspto-grants-1989_05
Patent number
US04831041

Reaction notes

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